Potassium Carbonate → HCID 86731262, compound

HRID 2277201Notes

Reaction equation

HRID 2277201 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[O:10][C:11]3[CH:17]=[C:16]([O:18][CH2:19][C@@H:20]([NH:22][C:23](=[O:25])[CH3:24])[CH3:21])[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:27][CH:28]1[CH2:30][C:29]1([F:32])[F:31].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[F:31][C:29]1([F:32])[CH2:30][CH:28]1[CH2:27][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[O:10][C:11]3[CH:17]=[C:16]([O:18][CH2:19][C@@H:20]([NH:22][C:23](=[O:25])[CH3:24])[CH3:21])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27614022-(Bromomethyl)-1,1-difluorocyclopropaneHCID 136341404HCID 136341404, compound

Product 1

HCID 86731262HCID 86731262, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of N-((2S)-1-((2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)acetamide (290 mg), 1-bromomethyl-2,2-difluorocyclopropane (288 mg) and potassium carbonate (175 mg) in DMF (10 mL) was stirred at 70° C. for 1 hr and 30 min. The reaction mixture was diluted with ethyl acetate, and washed with saturated brine, and the organic layer was subjected to silica gel column chromatography (NH, ethyl acetate), and the solvent was evaporated. The obtained solid was washed with diethyl ether to give the title compound (279 mg).

Workup

  1. washwashed with saturated brine
  2. customthe solvent was evaporated
  3. washThe obtained solid was washed with diethyl ether

Sources & evidence

ORD record
ord-210871ef9c9f4863aa77656ad553f651
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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