Potassium Carbonate → 3-[2-(4-Chloro-phenyl)-oxazol-4-ylmethoxy]-2,6-difluoro-benzamide

HRID 538567Notes

Reaction equation

HRID 538567 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[O:6][CH:7]=1.[F:15][C:16]1[C:24]([OH:25])=[CH:23][CH:22]=[C:21]([F:26])[C:17]=1[C:18]([NH2:20])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[O:6][CH:7]=[C:3]([CH2:2][O:25][C:24]3[C:16]([F:15])=[C:17]([C:21]([F:26])=[CH:22][CH:23]=3)[C:18]([NH2:20])=[O:19])[N:4]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 71315274-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazoleHCID 451201362,6-Difluoro-3-hydroxybenzamide

Product 1

HCID 594030313-[2-(4-Chloro-phenyl)-oxazol-4-ylmethoxy]-2,6-difluoro-benzamideYield 35.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-Chloromethyl-2-(4-chloro-phenyl)-oxazole (0.20 g, 0.87 mmol) in 2 ml of anhydrous DMF was added 2,6-Difluoro-3-hydroxy-benzamide (0.15 g, 0.78 mmol) and potassium carbonate (0.363 g, 2.60 mmol). The reaction mixture was stirred at 25° C. for 24 h under nitrogen atmosphere. The reaction mixture was evaporated to dryness under reduced pressure and the residue was purified by column chromatography on silica (60-120 M) using ethyl acetate/hexane (50:50) as the eluent to provide the title compound as white solid (0.10 g, 31%). 1H NMR (DMSO-d6, 400 MHz): δ 5.14 9s, 2H), 7.12 (t, J=9.20 Hz, 1H), 7.40 (m, 1H), 7.63 (d, J=8.40, 2H), 7.85 (br s, 1H), 8.0 (d, J=8.40 Hz, 2H), 8.13 (br s, 1H) and 8.36 (s, 1H). MS ES+ (365.13), HPLC (method I) Rt=16.36 min.

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. customthe residue was purified by column chromatography on silica (60-120 M)

Sources & evidence

ORD record
ord-95ad993b10e94bd7b814b4ca1cb48896
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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