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

HRID 902535ノート

反応式

HRID 902535 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6b1a905697f242cbbbd1874879763a8c
出典データセット
uspto-grants-2008_04
特許番号
US07365211B2

反応ノート

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