Potassium Carbonate → HCID 117665502, compound

HRID 1482452Notes

Reaction equation

HRID 1482452 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)=[C:13]2[C:17]=1[C:16](=[O:18])[CH:15]([C:19]([O:21][CH3:22])=[O:20])[CH2:14]2.Br[CH2:34][C:35]1[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=1>CC(C)=O.O>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:31])([F:30])[F:32])[CH:24]=2)=[C:13]2[C:17]=1[C:16](=[O:18])[C:15]([CH2:34][C:35]1[CH:36]=[CH:37][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:43][CH:44]=1)([C:19]([O:21][CH3:22])=[O:20])[CH2:14]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 117665483HCID 117665483, compound

Product 1

HCID 117665502HCID 117665502, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (15 mg, 0.11 mmol) was added to a solution of methyl 7-methoxy-1-oxo-4-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-2-carboxylate (26 mg, 0.07 mmol) in acetone (1.0 mL). Methyl 4-(bromomethyl)benzoate (32 mg, 0.14 mmol) was added and the mixture was stirred at room temperature. After 4 d, the reaction mixture was diluted with water (10 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (4 g column, hexanes→EtOAc, gradient) to afford 36 mg (98%) of methyl 7-methoxy-2-(4-(methoxycarbonyl)benzyl)-1-oxo-4-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-2-carboxylate.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude residue was purified by combiflash (4 g column, hexanes→EtOAc, gradient)

Sources & evidence

ORD record
ord-2aa18c05367c466fba6be7daac81d7e6
Source dataset
uspto-grants-2016_08
Patent number
US09415027B2

Reaction notes

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