Potassium Carbonate → 6-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

HRID 1790122

반응식

HRID 1790122 반응식
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C=O)C>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 242396-NitroindazoleHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

생성물 1

HCID 220366146-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A mixture of 6-nitroindazole (2.00 g, 12.3 mmol) and potassium carbonate (5.10 g 37.0 mmol) in DMF (40 mL) was stirred for 30 minutes, after which 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (3.20 g 18.9 mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature, filtered through a plug of silica gel and rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure and purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.61 (m, 4H), 2.47 (m, 4H), 2.90 (t, 2H, J=6.45), 4.68 (t, 2H, J=6.44), 7.94 (m, 1H), 8.00 (m, 1H), 8.31 (s, 1H), 8.77 (s, 1H); MS (DCI/NH3) m/z 261 [M+H]+.

후처리

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a plug of silica gel
  3. washrinsed with triethylamine/ethyl acetate (1/4)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30)

출처 및 근거

ORD 기록
ord-edc9cfd6a4df4fe9967ad41e06d4cd7c
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071182B2

연결된 노트

불러오는 중…