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[ CAS No. 609-12-1 ] {[proInfo.proName]}

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Chemical Structure| 609-12-1
Chemical Structure| 609-12-1
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Product Details of [ 609-12-1 ]

CAS No. :609-12-1 MDL No. :MFCD00026855
Formula : C7H13BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WNFUWONOILPKNX-UHFFFAOYSA-N
M.W : 209.08 Pubchem ID :79068
Synonyms :

Safety of [ 609-12-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P210-P234-P264-P280-P370+P378-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P406-P405 UN#:3265
Hazard Statements:H314-H227-H290 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 609-12-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 609-12-1 ]

[ 609-12-1 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 609-12-1 ]
  • [ 75279-55-9 ]
  • C15H19ClFNO2 [ No CAS ]
  • 2
  • [ 609-12-1 ]
  • [ 4435-14-7 ]
  • C15H27NO2 [ No CAS ]
  • 3
  • [ 609-12-1 ]
  • [ 75279-55-9 ]
  • [ 1044749-11-2 ]
  • 4
  • [ 609-12-1 ]
  • [ 22246-66-8 ]
  • [ 1448190-08-6 ]
YieldReaction ConditionsOperation in experiment
21% With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; for 18h;Inert atmosphere; Cooling with ice; Ethyl 2-(6-methoxy-l-oxoisoindolin-2-yI)-3-methylbutanoate Under an atmosphere of nitrogen, an ice-cooled solution of 6-methoxyisoindolin-l-one (commercially available from for example Astatech) (105 mg, 0.64 mmol) in DMF (2.5 mL) was treated with sodium hydride (60% w/w in mineral oil) (31 mg, 0.77 mmol) and the mixture was allowed to warm to ambient temperature. The mixture was then treated with ethyl 2-bromo-3-methylbutanoate (commercially available from for example Alfa Aesar) (135 mg, 0.64 mmol) and the mixture was stirred for 18 hours then cautiously treated with saturated aqueous ammonium chloride (20 mL). The product was extracted with ethyl acetate (2 x 25 mL) and the combined organic phase was washed with water (20 mL), brine (20 mL), filtered through a hydrophobic frit and evaporated to dryness. The product was purified by flash chromatography (20 g silica cartridge) using a gradient elution from 0 to 50% ethyl acetate in cyclohexane to afford the title compound (40 mg, 21% yield). LCMS RT= 1.03 min, ES+ve m/z 292 [M+H]+
21% With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; for 18h;Inert atmosphere; Cooling; Under an atmosphere of nitrogen, an ice-cooled solution of <strong>[22246-66-8]6-methoxyisoindolin-1-one</strong> (commercially available from for example Astatech) (105 mg, 0.64 mmol) in DMF (2.5 mL) was treated with sodium hydride (60% w/w in mineral oil) (31 mg, 0.77 mmol) and the mixture was allowed to warm to ambient temperature. The mixture was then treated with ethyl 2-bromo-3-methylbutanoate (commercially available from for example Alfa Aesar) (135 mg, 0.64 mmol) and the mixture was stirred for 18 hours then cautiously treated with saturated aqueous ammonium chloride (20 mL). The product was extracted with ethyl acetate (2*25 mL) and the combined organic phase was washed with water (20 mL), brine (20 mL), filtered through a hydrophobic fit and evaporated to dryness. the product was purified by flash chromatography (20 g silica cartridge) using a gradient elution from 0 to 50% ethyl acetate in cyclohexane to afford the title compound (40 mg, 21% yield). LCMS RT=1.03 min, ES+ve m/z 292 [M+H]+
  • 5
  • [ 609-12-1 ]
  • [ 22246-66-8 ]
  • [ 1448189-57-8 ]
  • 6
  • [ 609-12-1 ]
  • [ 21642-98-8 ]
  • ethyl 2-(3-cyano-4-methoxy-2-oxopyridin-1(2H)-yl)-3-methylbutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
6.11 g With caesium carbonate; In N,N-dimethyl-formamide; at 50℃; A) ethyl 2-(3-cyano-4-methoxy-2-oxopyridin-1(2H)-yl)-3-methylbutanoate (0774) A mixture of <strong>[21642-98-8]4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile</strong> (5.0 g), ethyl 2-bromo-3-methylbutanoate (10.4 g), cesium carbonate (32.6 g) and N,N-dimethylformamide (75 mL) was stirred at 50°C overnight. The reaction mixture was added to water, and the mixture was extracted twice with ethyl acetate. The extracts were combined, washed with water and then saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.11 g). MS (ESI+): [M+H]+ 279.2.
  • 7
  • [ 609-12-1 ]
  • [ 2105-96-6 ]
  • C13H16FNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67.7% With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 60℃; <strong>[2105-96-6]4-<strong>[2105-96-6]fluoro-3-nitrophenol</strong></strong> (500 mg, 3.18 mmol) was dissolved in DMF (6.365 mL) at room temperature. Cesium Carbonate (1244 mg, 3.82 mmol) was added followed by ethyl 2-bromo-3-methylbutanoate (0.574 mL, 3.50 mmol). The mixture was stirred at 60 °C. Reaction left at 60 °C overnight. Reaction was then diluted with water and a precipitate formed. The solid was filtered off and dried on high vacuum overnight to yield 83A (tan solid, 615 mg, 2.156 mmol, 67.7 percent yield), yield). LC-MS Anal. Calc'd for Ci3Hi6FN05 285.10, Tr = 1.04 min (Method A) (Note: product does not ionize well). NMR (400 MHz, MeOH-d4) delta: 7.60 (dd, J=6.0, 3.3 Hz, 1H), 7.53 (dd, J=10.9, 9.3 Hz, 1H), 7.38 (s, 1H), 4.84 (d, J=4.8 Hz, 1H), 4.16 (dd, J=7.1, 2.8 Hz, 2H), 2.20-2.30 (m, 1H), 1.15-1.20 (m, 3H), 1.01 (dd, J=6.8, 4.6 Hz, 6H) 83B.
  • 8
  • [ 609-12-1 ]
  • [ 4435-14-7 ]
  • [ 1268381-89-0 ]
YieldReaction ConditionsOperation in experiment
52.4 g of activated zinc powder and 450 ml of anhydrous THF,Add a few drops under N2 protectionEthyl alpha-bromoisovalerate2 to trigger the reaction,66 reflux 45min stirring until the reaction liquid becomes dark green after adding 20.324g (0.165mol)Cyclohexyl acetonitrile,And slowly add 2 (88.71 g, 0.4243 mol) within 1 h,Continue to reflow 1H stop heating, cooled to room temperature,Add 80ml 50% K2CO3 solution was stirred vigorously for 10min, the reaction solution was allowed to stratification, the organic phase was separated, the residue was extracted with THF,The combined organic phases were hydrolyzed by adding 150 ml of 15% HCl, the organic layer was separated and concentrated under reduced pressure, the aqueous layer was extracted three times with ethyl acetate,The combined organic phases were washed three times with saturated sodium bicarbonate solution, saturated NaCl, dried over anhydrous Na2SO4,The solvent was removed under reduced pressure to give compound 3 as a crude reddish brown liquid, 38.4 g, which was used directly in the next reaction without purification.
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