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CAS No. : | 153034-90-3 | MDL No. : | MFCD03095294 |
Formula : | C6H3ClINO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OPZCXONVRBYGHX-UHFFFAOYSA-N |
M.W : | 267.45 | Pubchem ID : | 10038637 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium hydroxide; iodine; In tetrahydrofuran; at 20℃; | Step 1. 2-chloro-4-iodonicotinonitrileTo 2-chloro-4-iodonicotinaldehyde (1.0 g, 3.7 mmol) dissolved in THF (11 mL) was added ammonium hydroxide (11 mL, 280 mmol) followed by iodine (1040 mg, 4.11 mmol), the reaction was held at ambient temperature 3.5 h, color visibly lightens as reaction progresses until the end when it is nearly colorless. LCMS indicates reaction to be complete. Reaction was quenched by addition of saturated NaHSO3, extracted into EtOAc. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide the crude product, 926 mg. Dissolved in CHCl3/MeOH and applied to 120 g silica gel column, the product fractions were concentrated in vacuo to give 728 mg product. The purified material was taken directly to next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With hydrazine hydrate; In ethanol; at 0 - 20℃; | To a solution of 2-chloro-4-iodonicotinaldehyde (101) (1.33 g, 5 mmol) in EtOH (10 mL), N2H4H2O (480 uL, 2 eq, 10 mmol) was added slowly at 0 - 5 °C. The solution was stirred at 10 °C for 1 h. Then additional amount of N2H4H2O (480 uL, 2 eq, 10 mmol) was added slowly and the resulting mixture was stirred at RT overnight. The mixture was concentrated in vacuo, brine (20 mL) was added and then extracted with ethyl acetate (3 * 50 mL). The combined organic layer was washed with brine (20 mL), dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to afford the crude product. |
19% | With hydrazine; In ethanol; at 20℃; for 15h; | Step 2:4-Chloro-lH-pyrazolo[4,3-c]pyridine To a mixture of 2-chloro-4-iodonicotinaldehyde (1.0 g, 3.7 mmol) in ethanol (6.0 mL) was added 3.0 mL of hydrazine (excess). The mixture was stirred at room temperature for 15 h and then concentrated under reduced pressure. The residue was diluted with water (30 mL) and extracted with dichloromethane (300 mL). The organic extract was washed with brine, dried over Na2S04, and concentrated under reduced pressure. The residue was dissolved in dichloromethane (5 mL) and stirred for 5 min. The precipitated solid was isolated by filtration and dried to give the desired intermediate 4-chloro-lH-pyrazolo[4,3-c]pyridine as a grey solid (110 mg, 19percent yield), which was used in the next step without further purification. LCMS(ESI) m/z: 154.1 [M+H+] |
With hydrazine; In ethanol; at 20℃; for 15h; | To a mixture of 2-chloro-4-iodonicotinaldehyde(1.0g, 3.7mmol) in ethanol(6.0 mL)was added 3.0mL of hydrazine (excess).The mixture was stirred atroom temperaturefor 15h and then concentrated under reduced pressure.The residue was diluted with water (30 mL)and extracted with dichloromethane (300 mL).The organic extract was washed with brine, dried over Na2SO4, and concentrated under reduced pressure.The residue was dissolved indichloromethane (5 mL)and stirred for 5 min. The precipitated solid was isolated by filtration and dried to give the desiredproductas a grey solid(110 mg, 19percent yield), which was used in the next step without further purification.LCMS(ESI) m/z: 154.1[M+H+]. |
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