Water → HCID 67492857, compound

HRID 384093Notes

Reaction equation

HRID 384093 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:3]=12.[H-].[Na+].[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O.[CH3:38]N(C=O)C>>[CH3:38][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:3]=12

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 178506295HCID 178506295, compound

Product 1

HCID 67492857HCID 67492857, compoundYield 99%

Conditions

Temperature
0 °C

Procedure

4-iodo-3-(trifluoromethyl)-1H-pyrazolo[5,4-b]pyridine (28.7 g, 91.69 mmol) was dissolved in dry DMF (300 mL). The mixture was cooled in an ice bath and sodium hydride (4.036 g, 100.9 mmol) was added portionwise over 10 minutes. The mixture was stirred at 0° C. for 30 minutes and then treated with trityl chloride (26.84 g, 96.27 mmol) in one portion. The reaction was allowed to warm to ambient and stirred for 16 hours. The reaction mixture was cooled in an ice bath and water (500 ml) was added slowly. The resultant solid was allowed to stir for 30 minutes and then filtered, washed with water and dried at 50° C. under high vacuum (50.5 g, 99% Yield).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. temperatureto warm to ambient and
  3. stirringstirred for 16 hours
  4. temperatureThe reaction mixture was cooled in an ice bath
  5. stirringto stir for 30 minutes
  6. filtrationfiltered
  7. washwashed with water
  8. customdried at 50° C. under high vacuum (50.5 g, 99% Yield)

Sources & evidence

ORD record
ord-5ade6818459942b18d7ebea8116b81f0
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

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