Sodium Carbonate → 7-(2,4-dichloro-phenyl)-1H-indazole

HRID 902535노트

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HRID 902535 반응식
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 203238997-Bromo-1H-indazole

생성물 1

HCID 686153577-(2,4-dichloro-phenyl)-1H-indazole

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

A solution of 7-bromo-1H-indazole (3; 1.01 g, 5.13 mmol) and tetrakis(triphenylphosphine) palladium(0) (0.176 g, 0.152 mmol) in 15 mL of ethylene glycol dimethyl ether was stirred for 30 m. To the solution was added 2,4-dichlorophenyl boronic acid (1.93 g, 10.1 mmol) and a 2 M aqueous Na2CO3 solution (7.1 mL, 14.2 mmol). The orange-yellow mixture was stirred at 80° C. for 19 h, allowed to cool, then partitioned between 50 mL of ethyl acetate and 50 mL of water. The organic layer was dried over MgSO4, filtered, and concentrated to an orange oil. Column chromatography (0→10% EtOAc/hexanes) afforded of 7-(2,4-dichloro-phenyl)-1H-indazole as a pale yellow foamy solid (4; 1.12 g, 83%).

후처리

  1. temperatureto cool
  2. custompartitioned between 50 mL of ethyl acetate and 50 mL of water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an orange oil

출처 및 근거

ORD 기록
ord-6b1a905697f242cbbbd1874879763a8c
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365211B2

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