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

HRID 1159970Notes

Reaction equation

HRID 1159970 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]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.ClC1N=C(C2C(C3C=C(NC(=O)C(F)(F)F)C=CC=3)=NN3C=CC=C(F)C=23)C=CN=1.[F:55][C:56]1[CH:64]=[CH:63][CH:62]=[C:61]([F:65])[C:57]=1[C:58](Cl)=[O:59].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:58](=[O:59])[C:57]4[C:56]([F:55])=[CH:64][CH:63]=[CH:62][C:61]=4[F:65])[CH:22]=[CH:23][CH:24]=3)=[N:10][N:11]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 874382,6-Difluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 577371983-[3-(2-Chloro-4-pyrimidinyl)-6-fluoropyrazolo[1,5-a]pyridin-2-yl]anilineHCID 86618783N-{3-[3-(2-chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide

Product 1

HCID 59513881N-{3-[3-(2-chloro-4-pyrimidinyl)-6-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamideYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 3-[3-(2-chloro-4-pyrimidinyl)-6-fluoropyrazolo[1,5-a]pyridin-2-yl]aniline (0.31 g) (prepared from N-{3-[3-(2-chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide obtained Example 168, Step B using a protocol similar to that described in Example 168, Step C) in THF (10 mL) was added 2,6-difluorobenzoyl chloride (0.19 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)-6-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide as a yellow solid (0.43 g, 96%). ESIMS (M+H)+=480.

Workup

  1. customobtained Example 168, Step B
  2. extractionAfter extraction with EtOAc (2×10 mL)
  3. dry with materialdrying with Na2SO4, and concentration
  4. customthe crude mixture was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-56054b86bf9f43e4b454ee1e9c110a60
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

Loading…