Water → 6-[6-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-3-nitropyridin-2-amine

HRID 510041Notes

Reaction equation

HRID 510041 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[NH:10][N:9]=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:5]2=[N:6][CH:7]=1.[H-].[Na+].Cl[C:22]1[N:27]=[C:26]([NH2:28])[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][CH:23]=1.O>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[N:10]([C:22]3[N:27]=[C:26]([NH2:28])[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][CH:23]=3)[N:9]=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 1785059746-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 666140776-[6-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-3-nitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

192 mg (approx. 0.517 mmol) of the compound from example 38A were dissolved in dimethylformamide (4 ml), then 34.5 mg (0.862 mmol) of sodium hydride (60% in mineral oil) were added and the mixture was stirred at RT for 30 min. Then 129 mg (0.744 mmol) of 6-chloro-3-nitropyridin-2-amine were added and the reaction mixture was stirred at RT for 1 h. The mixture was added to water, and the solids were filtered off, washed repeatedly with water and dried under high vacuum overnight. This gave 348 mg (85% purity, 84% of theory) of the title compound in solid form.

Workup

  1. stirringthe reaction mixture was stirred at RT for 1 h
  2. filtrationthe solids were filtered off
  3. washwashed repeatedly with water
  4. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-ad9a5028111145609c8a998a4a4b7796
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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