Potassium Carbonate → 5-nitro-1-(pyridin-2-ylmethyl)-1H-indazole

HRID 1162208

反応式

HRID 1162208 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].Cl.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=1)[N:8]=[CH:7]2)([O-:3])=[O:2]

参加物

6

反応物 3

HCID 11430Potassium Carbonate2 回HCID 215015-NitroindazoleHCID 23392Picolyl chloride hydrochloride2 回

生成物 1

HCID 224961495-nitro-1-(pyridin-2-ylmethyl)-1H-indazole収率 55%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

A mixture of 5-nitroindazole (40.75 g, 250 mmol), picolyl chloride hydrochloride (45.1 g, 275 mmol) and potassium carbonate (72.4 g, 525 mmol) in DMF (400 ml) was heated at 75° C. for 3 hours. Additional picolyl chloride hydrochloride (4.1 g, 25 mmol) and potassium carbonate (3.45 g, 25 mmol) were added and the mixture was heated at 75° C. for 2 additional hours. After cooling, the mixture was diluted with water (800 ml). The precipitate was filtered, washed with water and dried. The resulting solid was purified by chromatography on silica gel (eluant: 50% ethyl acetate in petroleum ether) to give 5-nitro-1-(pyridin-2-ylmethyl)-1H-indazole as a solid (34.5 g, 55%); NMR Spectrum (CDCl3) 5.77 (s, 2H), 7.03 (d, 1H), 7.23 (m, 1H), 7.55 (d, 1H), 7.63 (m, 1H), 8.27-8.23 (m, 2H), 8.58 (m, 1H), 8.74 (d, 1H); Mass spectrum MH+ 255.

後処理

  1. temperaturethe mixture was heated at 75° C. for 2 additional hours
  2. temperatureAfter cooling
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried
  6. customThe resulting solid was purified by chromatography on silica gel (eluant: 50% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-95e5fe9f4ba24f9cb02c2a372a67d2d6
出典データセット
uspto-grants-2010_10
特許番号
US07820683B2

関連ノート

読み込み中…