1,2-Dibromoethane → N-[1-(2-bromoethyl)-3-[5-chloro-2-(difluoromethoxy) phenyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 529780노트

반응식

HRID 529780 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH:26]([F:28])[F:27])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][NH:10][N:9]=2)[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:35][CH2:36][CH2:37]Br>O1CCCC1>[Br:35][CH2:36][CH2:37][N:10]1[CH:11]=[C:12]([NH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]3[CH:24]=[CH:23][CH:22]=[N:21][C:20]=23)=[O:15])[C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:25][CH:26]([F:28])[F:27])=[N:9]1

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 178522413HCID 178522413, 화합물

생성물 1

HCID 118522619N-[1-(2-bromoethyl)-3-[5-chloro-2-(difluoromethoxy) phenyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide수율 58%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

A mixture of N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (3.00 g, 7.41 mmol), Cs2CO3 (9.90 g, 30.38 mmol), tetrahydrofuran (90 mL), 1,2-dibromoethane (7.00 g, 37.26 mmol) was stirred at 70° C. for 3 hours in an oil bath. The mixture was allowed to cool to ambient temperature then concentrated under reduced pressure. The residue was purified by flash chromatography on silica eluting with ethyl acetate/petroleum ether (1:1) to afford N-[1-(2-bromoethyl)-3-[5-chloro-2-(difluoromethoxy)phenyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]-pyrimidine-3-carboxamide as a off-white solid (2.2 g, 58%). TLC: Rf=0.6; ethyl acetate/petroleum ether=1:1; LCMS (Method 14) [M+H]+=513.2, RT=1.03 min.

후처리

  1. temperatureto cool to ambient temperature
  2. concentrationthen concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica eluting with ethyl acetate/petroleum ether (1:1)

출처 및 근거

ORD 기록
ord-5c94be499ecf402bbab6201a59dc2303
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346815B2

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