Potassium Carbonate → HCID 86731252, compound

HRID 2277192Notes

Reaction equation

HRID 2277192 reaction equation
[F:1][C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:18])[CH:12]=3)=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:19][CH2:20][C@@H:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22].Br[CH2:28][CH:29]1[CH2:31][C:30]1([F:33])[F:32].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[F:32][C:30]1([F:33])[CH2:31][CH:29]1[CH2:28][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[O:9][C:10]3[C:2]([F:1])=[C:3]([O:19][CH2:20][C@@H:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])[CH:4]=[CH:5][C:6]=3[N:7]=2)=[CH:12][C:13]=1[F:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27614022-(Bromomethyl)-1,1-difluorocyclopropaneHCID 136341405HCID 136341405, compound

Product 1

HCID 86731252HCID 86731252, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of N-((2S)-1-((7-fluoro-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)acetamide (810 mg), 1-bromomethyl-2,2-difluorocyclopropane (573 mg) and potassium carbonate (463 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 (880 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-75b775d5d2cf455880f80c6975f72ee8
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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