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Cesium carbonate → Methyl 2-fluoro-4-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)benzoate

HRID 1257465
ノート
印刷プレビュー

反応式

HRID 1257465 の反応式
I[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:7]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[C:25]([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.O>[F:18][C:19]1[CH:20]=[C:21]([CH2:2][C:3]2[S:4][CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=3)[N:7]=2)[CH:22]=[CH:23][C:24]=1[C:25]([O:27][CH3:28])=[O:26]
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

5

反応物 3

HCID 10796Cesium carbonateHCID 27828183-Fluoro-4-(methoxycarbonyl)benzeneboronic acidHCID 66939273HCID 66939273、化合物

生成物 1

HCID 66939715Methyl 2-fluoro-4-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)benzoate

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
90 °C

実験手順

Under a nitrogen atmosphere, to a mixed solvent of the compound (270 mg, 0.72 mmol) obtained in Example 190c, 3-fluoro-4-methoxycarbonylphenylboronic acid (170 mg, 0.86 mmol) and cesium carbonate (1.2 g, 3.6 mmol) in tetrahydrofuran-water (v/v=5/1, 6 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (120 mg, 0.14 mmol), and the mixture was stirred at 90° C. overnight. The resulting salt was filtered and removed, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=75/25) to give the title compound as colorless crystals.

後処理

  1. filtrationThe resulting salt was filtered
  2. customremoved
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained crude product
  5. customwas purified by column chromatography (hexane-hexane/ethyl acetate=75/25)

出典と根拠

ORDレコード
ord-ccd1fc2be8874aeab2b31744999cc4fb
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08461348B2

反応ノート

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