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

HRID 2116660ノート

反応式

HRID 2116660 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b0d2143b3dd24e0ea9318cca743553e7
出典データセット
uspto-grants-2008_10
特許番号
US07439260B2

反応ノート

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