Potassium Carbonate → 5-(5-bromo-2-methylpyridin-3-yl)-1-methyl-1H-indazole

HRID 879544

反応式

HRID 879544 の反応式
[Br:1][C:2]1[C:3]([CH3:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.Br[CH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:21])[N:16]=[CH:15]2.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[N:16]=[CH:15]3)[C:3]([CH3:9])=[N:4][CH:5]=1.[Br:1][C:2]1[CH:7]=[C:11]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[N:16]=[CH:15]3)[CH:5]=[N:4][C:3]=1[CH3:9]

参加物

9

反応物 3

HCID 11430Potassium CarbonateHCID 6197053,5-Dibromo-2-methylpyridineHCID 497617045-(Bromomethyl)-1-methyl-1H-indazole

生成物 2

HCID 867003665-(5-bromo-2-methylpyridin-3-yl)-1-methyl-1H-indazoleHCID 867003675-(5-bromo-6-methylpyridin-3-yl)-1-methyl-1H-indazole

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
105 °C

実験手順

To a solution of 3,5-dibromo-2-methylpyridine (1.0 g, 3.99 mmol) and 5-(bromomethyl)-1-methyl-1H-indazole (772 mg, 4.38 mmol) in 1,4-dioxane (12 mL) was added Pd(PPh3)4 (231 mg, 0.20 mmol) and potassium carbonate solution (2 M aqueous, 6 mL, 12 mmol). The reaction mixture was stirred at 105° C. in a sealed tube for 1.5 h. The mixture was diluted with water (15 mL) and EtOAc (20 mL). The layers were separated, and the organic layer was dried, filtered, and concentrated in vacuo. The crude material was purified by CombiFlash (EtOAc w/5% MeOH and Hexanes) to give 5-(5-bromo-2-methylpyridin-3-yl)-1-methyl-1H-indazole and 5-(5-bromo-6-methylpyridin-3-yl)-1-methyl-1H-indazole.

後処理

  1. customThe layers were separated
  2. customthe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by CombiFlash (EtOAc w/5% MeOH and Hexanes)

出典と根拠

ORDレコード
ord-ca3fabd5a2aa4e58945490cc7b3a090f
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

関連ノート

読み込み中…