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

HRID 2116660노트

반응식

HRID 2116660 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b0d2143b3dd24e0ea9318cca743553e7
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07439260B2

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