Potassium Carbonate → 6-bromo-1-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1H-pyrrolo[3,2-b]pyridine

HRID 1404579노트

반응식

HRID 1404579 반응식
CS([O:5][CH:6]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([F:15])[C:9]=1[Cl:16])[CH3:7])(=O)=O.[Br:17][C:18]1[CH:19]=[C:20]([N+:35]([O-])=O)[C:21]([CH:24](C(OCC)=O)[C:25](OCC)=O)=[N:22][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:17][C:18]1[CH:19]=[C:20]2[N:35]([O:5][CH:6]([C:8]3[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([F:15])[C:9]=3[Cl:16])[CH3:7])[CH:25]=[CH:24][C:21]2=[N:22][CH:23]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 57516275HCID 57516275, 화합물HCID 585324961-(2,6-Dichloro-3-fluorophenyl)ethyl methanesulfonate

생성물 1

HCID 674584186-bromo-1-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1H-pyrrolo[3,2-b]pyridine수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 1-(2,6-dichloro-3-fluorophenyl)ethyl methanesulfonate (4.39 g, 15.3 mmol, 1.0 eq), 6-bromo-1H-pyrrolo[3,2-b]pyridin-1-ol (prepared as in example 1: 3.92 g, 20.0 mmol, 1.3 eq) and K2CO3 (6.34 g, 45.9 mmol, 3.0 eq) in 90 ml of N,N-dimethylformamide (DMF) was stirred at room temperature overnight. The solid was filtered out and the solvent evaporated. The residue was dissolved in DCM, and the solution was washed with water and brine, dried, evaporated and chromatographed (MeOH/DCM 1:20) to give a light yellow oil, 4.63 g, in 78% yield.

후처리

  1. filtrationThe solid was filtered out
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in DCM
  4. washthe solution was washed with water and brine
  5. customdried
  6. customevaporated
  7. customchromatographed (MeOH/DCM 1:20)
  8. customto give a light yellow oil, 4.63 g

출처 및 근거

ORD 기록
ord-b14a655b409c405baae399dddaf72956
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912330B2

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