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Cesium carbonate → HCID 58541696、化合物

HRID 600257
ノート
印刷プレビュー

反応式

HRID 600257 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([CH:15]=2)[CH:13]=[CH:12][S:11]3)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:22]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:27]=CC=C[CH:23]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:27]2[CH:22]=[CH:23][N:14]=[C:10]([S:11][CH3:12])[N:9]=2)[CH:13]=[CH:12][S:11]3)=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 8681986-(4-Fluorophenyl)imidazo[2,1-b][1,3]thiazole

生成物 1

HCID 58541696HCID 58541696、化合物

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 6-(4-fluorophenyl)-imidazo[2,1-b]thiazole (J) (6.0 g, 27.6 mmol), 4-iodo-2-thiomethylpyrimidine (10.4 g, 41.3 mmol), cesium carbonate (13.4 g, 41.3 mmol), triphenylphosphine (2.88 g, 11 mmol), and palladium acetate (1.22 g, 5.5 mmol) is added anhydrous dimethylformamide (60 mL). The reaction mixture is sealed and shaken at 80° C. for 12 hours. The reaction was quenched by addition of water (200 mL). The aqueous layer is extracted with ethyl acetate (3×100 mL). The organic phase is washed sequentially with water (100 mL) and a saturated aqueous, sodium chloride solution (100 mL). The organic phase is dried over sodium sulfate, filtered, and the solvent evaporated in vacuo. The crude product is purified by silica gel column chromatography, eluting with a gradient of ethyl acetate/hexane (20-30%). After evaporation of the solvent, 6-(4-fluorophenyl)-5-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[2,1-b]thiazole (K) (Compound CXXXIX, Table 2) is obtained as a white solid (3.5 g, 37%) m.p. 151-152° C.;

後処理

  1. customThe reaction mixture is sealed
  2. customThe reaction was quenched by addition of water (200 mL)
  3. extractionThe aqueous layer is extracted with ethyl acetate (3×100 mL)
  4. washThe organic phase is washed sequentially with water (100 mL)
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customThe crude product is purified by silica gel column chromatography
  9. washeluting with a gradient of ethyl acetate/hexane (20-30%)
  10. customAfter evaporation of the solvent

出典と根拠

ORDレコード
ord-50ce19b79f934a8b8f52a6f55ac7f09f
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07902192B2

反応ノート

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