N-[5-(2-Bromo-pyridin-4-yl)-4-methyl-thiazol-2-yl]-2,6-difluoro-benzamide → 2,6-Difluoro-N-(4-methyl-5-(pyridin-4-yl)thiazol-2-yl)benzamide hydrobromide

HRID 1255120Notes

Reaction equation

HRID 1255120 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:23])[C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])=[N:10][C:9]=2[CH3:24])[CH:5]=[CH:4][N:3]=1.[H][H]>C(O)C.[Pd]>[BrH:1].[F:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([F:21])[C:15]=1[C:14]([NH:13][C:11]1[S:12][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[CH:2][CH:7]=2)=[C:9]([CH3:24])[N:10]=1)=[O:23]

Participants

5

Reactant 2

HCID 24765026N-[5-(2-Bromo-pyridin-4-yl)-4-methyl-thiazol-2-yl]-2,6-difluoro-benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 247654032,6-Difluoro-N-(4-methyl-5-(pyridin-4-yl)thiazol-2-yl)benzamide hydrobromide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a solution of Compound 27 (21.0 mg, 0.05 mmol) in ethanol (2.0 mL) was added 10% Pd/C (10.0 mg). The mixture was stirred under 1 atmosphere of hydrogen for overnight. The mixture was filtered through a short plug of silica to give Compound 54, 19.4 mg, 92%) as a white solid.

Workup

  1. filtrationThe mixture was filtered through a short plug of silica

Sources & evidence

ORD record
ord-ad7b00c22f3243e48264612a5b92b75f
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

Loading…