Water → 1-[5-(difluoromethyl)pyridin-2-yl]-1H-pyrrole-3-carboxylic acid tert-butyl ester

HRID 1748477노트

반응식

HRID 1748477 반응식
[H-].[Na+].[C:3]([O:7][C:8]([C:10]1[CH:14]=[CH:13][NH:12][CH:11]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[C:16]1[CH:21]=[CH:20][C:19]([CH:22]([F:24])[F:23])=[CH:18][N:17]=1.O>CN(C)C=O>[C:3]([O:7][C:8]([C:10]1[CH:14]=[CH:13][N:12]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]([F:24])[F:23])=[CH:18][N:17]=2)[CH:11]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11171190tert-butyl 1H-pyrrole-3-carboxylateHCID 547722752-Bromo-5-(difluoromethyl)pyridine

생성물 1

HCID 866924421-[5-(difluoromethyl)pyridin-2-yl]-1H-pyrrole-3-carboxylic acid tert-butyl ester수율 71.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (230 mg) was added to a solution of 1H-pyrrole-3-carboxylic acid tert-butyl ester (804 mg) in N,N-dimethylformamide (9.6 ml) at room temperature and stirred at the same temperature for 0.5 hour. 2-Bromo-5-(difluoromethyl)pyridine (1.0 g) was added and stirred at 60° C. for an hour. After completion of the reaction, the reaction solution was cooled to room temperature, water was added and the precipitated solid was filtered. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-[5-(difluoromethyl)pyridin-2-yl]-1H-pyrrole-3-carboxylic acid tert-butyl ester (1.01 g) as a white solid.

후처리

  1. stirringstirred at 60° C. for an hour
  2. customAfter completion of the reaction
  3. filtrationthe precipitated solid was filtered
  4. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-28bafb48d49d4dc4b6579cae3148053e
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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