N-methyl-2-pyrrolidone → Potassium Hydroxide

HRID 559645Notes

Reaction equation

HRID 559645 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:10])[C:7]=1[CH:8]=[O:9].Cl.[F:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.CN1C(=O)CCC1.[OH-].[K+:29]>O>[OH-:9].[K+:29].[Br:10][C:6]1[CH:5]=[N:4][CH:3]=[C:2]2[N:19]([C:16]3[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=3)[N:20]=[CH:8][C:7]=12

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 14797Potassium Hydroxide2×HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 27629983,5-Dibromo-4-pyridinecarboxaldehyde

Product 2

HCID 14797Potassium HydroxideHCID 592784604-Bromo-1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 1 L flask was charged 3,5-dibromopyridine-4-carboxaldehyde (50.0 g, 188.7 mmol, 1.0 eq) and 4-fluorophenylhydrazine hydrochloride (31.0 g, 190.7 mmol, 1.01 eq). NMP (250 mL) was charged, and the resulting slurry was stirred at ambient temperature for 2 hours. A solution of aqueous KOH was prepared from 85% KOH pellets (27.4 g, 415.2 mmol, 2.2 eq) and water (27.4 mL), and this KOH solution was charged to the reaction mixture. The batch was heated to 80° C. and held at this temperature for 30-60 minutes. Water (250 mL) was then charged at 80° C., and the resulting slurry was cooled to ambient temperature over 4-16 hours. The slurry was filtered, the solid was washed with water, and oven dried under vacuum to afford 4-bromo-1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine as a tan colored solid, 51.5 g, 99.3 area % purity by HPLC, 93% yield.

Workup

  1. temperatureThe batch was heated to 80° C.
  2. waitheld at this temperature for 30-60 minutes
  3. temperaturethe resulting slurry was cooled to ambient temperature over 4-16 hours
  4. filtrationThe slurry was filtered
  5. washthe solid was washed with water, and oven
  6. customdried under vacuum

Sources & evidence

ORD record
ord-61695b2ec80e4d688c3ba35e72f7a392
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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