Cesium carbonate → 1-[2-(4-tert-butyl-phenyl)-2-oxo-ethyl]-4-fluoro-1H-pyrrole-2-carboxylic acid methyl ester

HRID 2272965ノート

反応式

HRID 2272965 の反応式
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[C:8]([F:10])[CH:9]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=1)=[O:20]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=2)=[O:20])[CH:7]=[C:8]([F:10])[CH:9]=1)=[O:4]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 23247702-Bromo-1-(4-tert-butylphenyl)ethan-1-oneHCID 45089983methyl 4-fluoro-1H-pyrrole-2-carboxylate

生成物 1

HCID 898261481-[2-(4-tert-butyl-phenyl)-2-oxo-ethyl]-4-fluoro-1H-pyrrole-2-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A suspension of 93.7 mg (0.655 mmol) 4-fluoro-1H-pyrrole-2-carboxylic acid methyl ester (synthesis described in J. Leroy et al. Tetrahedron 58, p. 6713, 2002) and 640 mg (1.96 mmol) cesium carbonate in 1.3 ml DMF is heated to 50° C. under stirring. 167 mg (0.655 mmol) 2-bromo-1-(4-tert-butyl-phenyl)ethanone is added and the reaction mixture is stirred for 18 hours at 50° C. The reaction mixture is filtered with suction and the filtrate is evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 1-[2-(4-tert-butyl-phenyl)-2-oxo-ethyl]-4-fluoro-1H-pyrrole-2-carboxylic acid methyl ester as brown amorphous solid; HPLC/MS 3.26 min (B), [M+H] 318.

後処理

  1. stirringthe reaction mixture is stirred for 18 hours at 50° C
  2. filtrationThe reaction mixture is filtered with suction
  3. customthe filtrate is evaporated
  4. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

出典と根拠

ORDレコード
ord-b387f023f7614cdb9e5128b9f9fc5b50
出典データセット
uspto-grants-2015_09
特許番号
US09120805B2

反応ノート

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