Potassium Carbonate → 4-(3,5-difluorophenyl)-7-({5-[1-hydroxy-1-(trifluoromethyl)propyl]-1,3-thiazol-2-yl}thio)-2H-chromen-2-one

HRID 2116660Notes

Reaction equation

HRID 2116660 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[O:12][C:11](=[O:19])[C:10]=2F)[CH:5]=[C:6]([F:8])[CH:7]=1.[F:21][C:22]([F:34])([F:33])[C:23]([C:27]1[S:31][C:30]([SH:32])=[N:29][CH:28]=1)([OH:26])[CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([S:32][C:30]4[S:31][C:27]([C:23]([OH:26])([C:22]([F:21])([F:33])[F:34])[CH2:24][CH3:25])=[CH:28][N:29]=4)=[CH:16][CH:17]=3)[O:12][C:11](=[O:19])[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866052174-(3,5-difluorophenyl)-fluoro-2H-chromen-2-oneHCID 178458806HCID 178458806, compound

Product 1

HCID 598148564-(3,5-difluorophenyl)-7-({5-[1-hydroxy-1-(trifluoromethyl)propyl]-1,3-thiazol-2-yl}thio)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-(3,5-difluorophenyl)-fluoro-2H-chromen-2-one (0.258 g, 0.93 mmol), 1,1,1-trifluoro-2-(2-mercapto-1,3-thiazol-5-yl)butan-2-ol, (0.250 g, 1.03 mmol) and potassium carbonate (0.387 g, 2.8 mmol) in NMP was heated at 120° C. overnight. The mixture was cooled to room temperature and partitioned between aqueous NH4Cl and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with water, brine and dried over anhydrous Na2SO4. The solvent was evaporated and the residue chromatographed on silica gel (toluene/acetone; 95:5) to give the title compound. 1H NMR (400 MHz, CDCl3): δ 7.78 (s, 1H), 7.56 (d, 1H), 7.43 (d, 1H), 7.37 (dd, 1H), 7.00-7.04 (m, 3H), 6.41 (s, 1H), 2.66 (br s, 1H), 2.12 (q, 2H), 0.98 (t, 3H).

Workup

  1. custompartitioned between aqueous NH4Cl and EtOAc
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was evaporated
  7. customthe residue chromatographed on silica gel (toluene/acetone; 95:5)

Sources & evidence

ORD record
ord-b0d2143b3dd24e0ea9318cca743553e7
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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