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[ CAS No. 99455-05-7 ] {[proInfo.proName]}

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Chemical Structure| 99455-05-7
Chemical Structure| 99455-05-7
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Product Details of [ 99455-05-7 ]

CAS No. :99455-05-7 MDL No. :MFCD11847805
Formula : C10H8BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :KBTKKEMYFUMFSJ-UHFFFAOYSA-N
M.W : 238.08 Pubchem ID :10657538
Synonyms :

Safety of [ 99455-05-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 99455-05-7 ]

* 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 [ 99455-05-7 ]

[ 99455-05-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 26421-44-3 ]
  • [ 99455-05-7 ]
  • (6-bromo-2-methoxyquinolin-3-yl)(2,5-dimethylthiophen-3-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% A solution of 2,2,6,6-tetramethylpiperidine (1.89 mL, 11.1 mmol) in dry THF (12 mL) was cooled to -40 C, and -BuLi (4.45 mL of a 2.5N solution in hexane, 11.1 mmol) was added and the solution was stirred at -40 C for 15 min, then cooled to -78 C. A solution of 6-bromo- 2-methoxyquinoline (2.20 g, 9.28 mmol) in THF (10 mL) was added dropwise, and the orange solution was stirred at -78 C for 1.5 h, then a solution of 12 (1.30 g, 9.27 mmol) in THF (10 mL) was added. The mixture was stirred at -78 C for 3 h, then acetic acid (1.60 mL, 28.0 mmol) was added and the solution was allowed to warm to r. . The mixture was partitioned between EtOAc and water, and the organic fraction was dried and evaporated. Chromatography with DCM:hexanes (1 :3) eluted starting materials, then elution with DCM:hexanes (1 : 1) gave 13 as a white solid (1.97 g, 56%). 1H MR (CDC13) δ 7.93 (s, 1H), 7.88 (d, J = 2.1 Hz, 1H), 7.70 (d, J = 8.4 Hz, 1H), 7.65 (dd, J = 8.4, 2.1 Hz, 1H), 6.51 (d, J = 1.0 Hz, 1H), 6.04 (dd, J = 3.3, 0.8 Hz, 1H), 4.07 (s, 3H), 2.67 (d, J = 3.4 Hz, 1H), 2.43 (s, 3H), 2.34 (s, 3H). Found: [M+H]=378.2
56% Asolution of 2,2,6,6-tetramethylpiperidine (1.89 mL, 11.1 mmol) in dryTHF (12 mL) was cooled to -40 C, n-BuLi(4.45 mL of a 2.5N solution in hexane, 11.1 mmol) was added and the solutionwas stirred at -40 C for 15 min, then cooled to -78 C. A solution of 6-bromo-2-methoxyquinoline(51) (2.20 g, 9.28 mmol) in THF (10mL) was added dropwise, the orange solution was stirred at -78 C for 1.5 h,then a solution of 2,5-dimethylthiophene-3-carbaldehyde (52) (1.30 g, 9.27 mmol) in THF (10 mL) was added. The mixture was stirred at -78 C for 3 h,then acetic acid (1.60 mL, 28.0 mmol) was added and the solution was allowed towarm to r.t.. The mixture waspartitioned between EtOAc and water, and the organic fraction was dried andevaporated. Chromatography with DCM:hexanes (1:3) eluted starting materials,then elution with DCM:hexanes (1:1) gave6-bromo-2-methoxyquinolin-3-yl)(2,5-dimethylthiophen-3-yl)methanol (53) as a white solid (1.97 g, 56%).M.p. 119-122 C. 1H NMR (CDCl3) δ 7.93 (s, 1H), 7.88 (d, J = 2.1 Hz, 1H), 7.70 (d, J = 8.4 Hz, 1H), 7.65 (dd, J = 8.4, 2.1 Hz, 1H), 6.51 (d, J = 1.0 Hz, 1H), 6.04 (dd, J = 3.3, 0.8 Hz, 1H), 4.07 (s, 3H), 2.67(d, J = 3.4 Hz, 1H), 2.43 (s,3H), 2.34 (s, 3H). Found: [M+H]=378.2.
  • 2
  • [ 54439-75-7 ]
  • [ 99455-05-7 ]
  • C18H15BrClNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Compound V (17.0 g, 0.1 mol) was added to a 500 mL three-necked flask, and tetrahydrofuran (100 mL) was added thereto, and stirring was started. Under a nitrogen atmosphere, tetramethylammonium lithium (LTMP) (44 mL, 0.1) was added dropwise at -40 °C. Lmol), after the addition is completed, continue to low temperatureStir for 0.5 hours,Then, a solution of 2,3-difluorobenzaldehyde (16.6 g, 0.1 mol) in tetrahydrofuran was added dropwise, and the reaction was continued at -40 ° C for 1 hour.TLC point plate monitoring, after the disappearance of the raw material point, a saturated ammonium chloride solution was added dropwise below zero degree, ethyl acetate was added, and the organic layer was separated, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. Yellow solid compound IV-4, 33.9 g, yield 83percent.
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