Potassium Carbonate → HCID 90417976, compound

HRID 2177264Notes

Reaction equation

HRID 2177264 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([Cl:20])=[N:9][S:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][CH:13]=1)(=O)=O.[F:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:25]=[C:26]([F:29])[C:27]=1O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:20][C:8]1[C:7]([CH2:6][O:5][C:27]2[C:26]([F:29])=[CH:25][C:24]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:23][C:22]=2[F:21])=[C:11]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][CH:13]=2)[S:10][N:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 90418885HCID 90418885, compound

Product 1

HCID 90417976HCID 90417976, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Into a 50-mL round-bottom flask, was placed [3-chloro-5-(4-ethylphenyl)-1,2-thiazol-4-yl]methyl methanesulfonate (20 mg, 0.05 mmol, 1.00 equiv), ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate (16 mg, 0.07 mmol, 1.20 equiv), potassium carbonate (25 mg, 0.18 mmol, 3.00 equiv), N,N-dimethylformamide (2 mL). The resulting solution was stirred overnight at 25° C. The reaction was then quenched by the addition of 5 mL of water. The resulting solution was extracted with 3×5 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1×10 mL of brine. The mixture was dried over anhydrous sodium sulfate. The residue was applied onto the TLC with ethyl acetate/petroleum ether (1:15). This resulted in 20 mg (71%) of ethyl 3-(4-[[3-chloro-5-(4-ethylphenyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)propanoate as colorless oil.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of 5 mL of water
  3. extractionThe resulting solution was extracted with 3×5 mL of ethyl acetate
  4. washThe resulting mixture was washed with 1×10 mL of brine
  5. dry with materialThe mixture was dried over anhydrous sodium sulfate
  6. customThis resulted in 20 mg (71%) of ethyl 3-(4-[[3-chloro-5-(4-ethylphenyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)propanoate as colorless oil

Sources & evidence

ORD record
ord-88f03c7251094307a25146127ea86d37
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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