HCID 86728475, compound → HCID 86728476, compound

HRID 1752966Notes

Reaction equation

HRID 1752966 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])[CH:16]=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:13]C)[CH:8]=1)=[O:5]>Br.C(O)(=O)C.O>[F:1][C:2]1[CH:18]=[C:17]([C:19]([F:25])([F:24])[C:20]([F:21])([F:23])[F:22])[CH:16]=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=1)=[O:5]

Participants

5

Reactant 1

HCID 86728475HCID 86728475, compound

Product 1

HCID 86728476HCID 86728476, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2-fluoro-N-(2-methoxy-4-pyridyl)-4-(1,1,2,2,2-pentafluoroethyl)benzamide (200 mg, 0.55 mmol) in HBr in acetic acid (1.3 mL of 33% w/v, 5.49 mmol) was stirred at 100° C. for 2 hours, at this time 1 ml of HBr in acetic acid (33% w/v) was added and the mixture was stirred at 100° C. for 4 hours, then cooled to room temperature. The reaction mixture was diluted with water and a precipitate formed. The precipitate was filtered off, washed with water (2×), cold methyl-tert-butyl ether and dried under vacuum to give 2-fluoro-N-(2-oxo-1H-pyridin-4-yl)-4-(1,1,2,2,2-pentafluoroethyl)benzamide (138 mg, 72%) as a light grey solid. ESI-MS m/z calc. 350.05, found 351.3 (M+1)+; Retention time: 1.3 minutes (3 minutes run).

Workup

  1. additionwas added
  2. temperaturecooled to room temperature
  3. customa precipitate formed
  4. filtrationThe precipitate was filtered off
  5. washwashed with water (2×), cold methyl-tert-butyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c889af3336ec4eef9a60af44c743b268
Source dataset
uspto-grants-2015_10
Patent number
US09163042B2

Reaction notes

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