Dimethylformamide → HCID 90417623, compound

HRID 2177281Notes

Reaction equation

HRID 2177281 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([Cl:19])=[N:9][S:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)(=O)=O.[F:20][C:21]1[CH:22]=[C:23]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:24]=[C:25]([F:28])[C:26]=1O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:19][C:8]1[C:7]([CH2:6][O:5][C:26]2[C:25]([F:28])=[CH:24][C:23]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:22][C:21]=2[F:20])=[C:11]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[S:10][N:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 90418018HCID 90418018, compound

Product 1

HCID 90417623HCID 90417623, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Into a 50-mL round-bottom flask, was placed [3-chloro-5-(4-chlorophenyl)-1,2-thiazol-4-yl]methyl methanesulfonate (320 mg, 0.95 mmol, 1.00 equiv), ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate (230 mg, 1.00 mmol, 1.06 equiv), potassium carbonate (420 mg, 3.04 mmol, 3.21 equiv), N,N-dimethylformamide (10 mL). The resulting solution was stirred overnight at 30° C. The resulting solution was diluted with of H2O. The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (17/83). The collected fractions were combined and concentrated under vacuum. This resulted in 340 mg (68%) of ethyl 3-(4-[[3-chloro-5-(4-chlorophenyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)propanoate as colorless oil. Mass spectrum (ESI, m/z): Calcd. for C21H17C12F2NO3S, 472.0 (M+H). found 472.0.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with 3×10 mL of ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 340 mg (68%) of ethyl 3-(4-[[3-chloro-5-(4-chlorophenyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)propanoate as colorless oil

Sources & evidence

ORD record
ord-a67487f0906947b1803f0c661ab3089a
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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