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

HRID 2272965노트

반응식

HRID 2272965 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b387f023f7614cdb9e5128b9f9fc5b50
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120805B2

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