2,6-Difluorobenzoyl chloride → N-{3-[3-(2-chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide

HRID 1159968Notes

Reaction equation

HRID 1159968 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=3)[NH2:21])=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=23)[CH:5]=[CH:4][N:3]=1.[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:27]=1[C:28](Cl)=[O:29].C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:19]=[C:20]([NH:21][C:28](=[O:29])[C:27]4[C:26]([F:25])=[CH:34][CH:33]=[CH:32][C:31]=4[F:35])[CH:22]=[CH:23][CH:24]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=23)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 874382,6-Difluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 595114323-[3-(2-Chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]aniline

Product 1

HCID 59513844N-{3-[3-(2-chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamideYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[3-(2-chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]aniline (0.31 g) in THF (10 mL) was added 2,6-difluorobenzoyl chloride (0.18 g). The reaction was kept stirring at rt for 0.5 h and worked up with sat. NaHCO3 solution (8 mL). After extraction with EtOAc (2×10 mL), drying with Na2SO4, and concentration, the crude mixture was purified through silica gel column chromatography to afford N-{3-[3-(2-chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide as a yellow solid (0.42 g, 95%). ESIMS (M+H)+=480.

Workup

  1. extractionAfter extraction with EtOAc (2×10 mL)
  2. dry with materialdrying with Na2SO4, and concentration
  3. customthe crude mixture was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-030290dfa5964364bdf1bb80463292c1
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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