Sodium Carbonate → 2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-6-(2-chloro-phenyl)-3H-imidazo[4,5-c]pyridine

HRID 570277노트

반응식

HRID 570277 반응식
Br[C:2]1[N:7]=[CH:6][C:5]2[NH:8][C:9]([C:11]3[N:12]([CH3:20])[N:13]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:15]=3)=[N:10][C:4]=2[CH:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[C:16]([C:14]1[CH:15]=[C:11]([C:9]2[NH:8][C:5]3[CH:6]=[N:7][C:2]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[Cl:21])=[CH:3][C:4]=3[N:10]=2)[N:12]([CH3:20])[N:13]=1)([CH3:19])([CH3:18])[CH3:17]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 1363374486-bromo-2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3H-imidazo[4,5-c]pyridine

생성물 1

HCID 1360731782-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-6-(2-chloro-phenyl)-3H-imidazo[4,5-c]pyridine

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

A solution of 6-bromo-2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3H-imidazo[4,5-c]pyridine (50 mg, 0.15 mmol, prepared as described in the previous step), 2-chlorophenylboronic acid (47 mg, 0.30 mmol), 2M Na2CO3 (0.60 mL, 1.2 mmol) and DME (1 mL) was stirred at 90° C. for 18 h. The resulting mixture was allowed to cool to room temperature and organic layer was separated. The organic layer was purified by direct application to silica preparative TLC plates (2000 micron) and eluted with 3:7 EtOAc-hexanes to yield 2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-6-(2-chloro-phenyl)-3H-imidazo[4,5-c]pyridine.

후처리

  1. temperatureto cool to room temperature
  2. customorganic layer was separated
  3. customThe organic layer was purified by direct application to silica preparative TLC plates (2000 micron)
  4. washeluted with 3:7 EtOAc-hexanes

출처 및 근거

ORD 기록
ord-c63c5e8c2c4d40af8f17ef409e3741d8
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023846B2

반응 노트

불러오는 중…