Potassium Carbonate → 5-nitro-1-(2-piperidin-1-yl-ethyl)-1H-indazole

HRID 1790118

反応式

HRID 1790118 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[N:8]=[CH:7]2)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochloride

生成物 1

HCID 114927965-nitro-1-(2-piperidin-1-yl-ethyl)-1H-indazole収率 65.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 5-nitroindazole (4.0 g, 24 mmol) and potassium carbonate (10 g 74 mmol) in DMF (60 mL) was stirred for 30 minutes after which 1-(2-chloro-ethyl)-piperidine hydrochloride (6.8 g 37 mmol) was added. The mixture was heated to 60° 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 filtrate was concentrated under reduced pressure and purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30) to provide the title compound (4.3 g, 64% yield). 1H NMR (300 MHz, DMSO-d6) ppm 1.34 (m, 6H), 2.36 (m, 4H), 2.72 (t, J=6.44, 2H), 4.58 (t, J=6.44, 2H), 7.90 (m, 1H), 8.21 (m, 1H), 8.40 (m, 1H), 8.82 (m, 1H); MS (DCI/NH3) m/z 275 [M+H]+.

後処理

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

出典と根拠

ORDレコード
ord-cfc872f545334002b7cc706c5cd6d8bf
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…