Dimethylformamide → HCID 90418851, compound

HRID 2177390Notes

Reaction equation

HRID 2177390 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=2)=[N:9][S:10][C:11]=1[C:12]([F:15])([F:14])[F:13])(=O)=O.O[C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[CH:30]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:29][CH2:28]2.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:22]([C:19]1[CH:20]=[CH:21][C:16]([C:8]2[C:7]([CH2:6][O:5][C:25]3[CH:26]=[C:27]4[C:31](=[CH:32][CH:33]=3)[CH:30]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:29][CH2:28]4)=[C:11]([C:12]([F:15])([F:14])[F:13])[S:10][N:9]=2)=[CH:17][CH:18]=1)[CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23529437Ethyl 2-(5-hydroxy-2,3-dihydro-1h-inden-1-yl)acetateHCID 90418592HCID 90418592, compound

Product 1

HCID 90418851HCID 90418851, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Into a 50-mL round-bottom flask, was placed [3-(4-ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methyl methanesulfonate (160 mg, 0.44 mmol, 1.00 equiv), ethyl 2-(5-hydroxy-2,3-dihydro-1H-inden-1-yl)acetate (97 mg, 0.44 mmol, 1.01 equiv), potassium carbonate (183 mg, 1.32 mmol, 3.02 equiv), N,N-dimethylformamide (3 mL). The resulting solution was stirred overnight at 30° C. The resulting solution was diluted with 20 mL of H2O. The resulting mixture was washed with 3×20 mL of sodium chloride. The mixture was dried over anhydrous sodium sulfate. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (15:85). This resulted in 200 mg (93%) of ethyl 2-(5-[[3-(4-ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-2,3-dihydro-1H-inden-1-yl)acetate as colorless oil.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. washThe resulting mixture was washed with 3×20 mL of sodium chloride
  3. dry with materialThe mixture was dried over anhydrous sodium sulfate
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThis resulted in 200 mg (93%) of ethyl 2-(5-[[3-(4-ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-2,3-dihydro-1H-inden-1-yl)acetate as colorless oil

Sources & evidence

ORD record
ord-c71c895c0a31415f89bc5ae71f7a7c83
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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