Potassium Carbonate → 3-chloro-6-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

HRID 1790168

反応式

HRID 1790168 の反応式
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C=O)C>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[N:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 816691-(2-Chloroethyl)pyrrolidineHCID 178526457HCID 178526457、化合物

生成物 1

HCID 220365773-chloro-6-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole収率 66%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 3-chloro-6-nitro-1H-indazole (2.4 g, 12 mmol) was treated with potassium carbonate (5.0 g, 36 mmol) in DMF (40 mL) for about 30 minutes, after which 1-(2-chloro-ethyl)-pyrrolidine (3.1 g, 18 mmol) was added. The mixture was heated to 50° C. for 6 hours, cooled to room temperature and filtered through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4). The combined filtrate was concentrated under reduced pressure and purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30) to provide the title compound (2.3 g, 66%). 1H NMR (300 MHz, DMSO-d6) ppm 1.61 (m, 4H), 2.47 (m, 4H), 2.89 (t, J=6.44, 2H), 4.67 (t, J=6.44, 2H), 7.90 (m, 1H), 8.01 (m, 1H), 8.86 (m, 1H); MS (DCI/NH3) m/z 295 [M+H]+.

後処理

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

出典と根拠

ORDレコード
ord-89fd0e5818a94079863ca5d75b90b759
出典データセット
uspto-grants-2006_07
特許番号
US07071182B2

関連ノート

読み込み中…