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

HRID 879544노트

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HRID 879544 반응식
[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]

참가 물질

9

반응물 3

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

생성물 2

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
105 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ca3fabd5a2aa4e58945490cc7b3a090f
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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