Sodium Carbonate → N-cyclopropyl-3-(1H-indazol-5-yl)-4-methylbenzamide

HRID 1988923ノート

反応式

HRID 1988923 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C(OC(C)(C)C)=O)[N:6]=[CH:5]2.[CH:18]1([CH2:21][NH:22][C:23](=[O:39])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[CH2:20]C1.[C:40](=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>[CH:21]1([NH:22][C:23](=[O:39])[C:24]2[CH:25]=[CH:26][C:27]([CH3:40])=[C:28]([C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[NH:7][N:6]=[CH:5]4)[CH:29]=2)[CH2:18][CH2:20]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 228320255-Bromo-1H-indazole, N1-BOC protected2 回HCID 68676775HCID 68676775、化合物2 回

生成物 1

HCID 10469531N-cyclopropyl-3-(1H-indazol-5-yl)-4-methylbenzamide

試薬・触媒・溶媒 2

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

実験手順

To a solution of tert-butyl 5-bromo-1H-indazole-1-carboxylate (Intermediate 3, 2.0 g) and N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 5, 2.04 g) in DME (125 ml) was added tetrakis (triphenylphosphine) palladium (0.78 g) and aqueous sodium carbonate (1M, 80 ml). The mixture was heated at reflux under nitrogen for 16 h. The solvent was evaporated and the residue was purified by column chromatography on silica, eluting with cyclohexane:ethyl acetate (2:1 to 1:1) to give the title compound (1.38 g).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen for 16 h
  3. customThe solvent was evaporated
  4. customthe residue was purified by column chromatography on silica
  5. washeluting with cyclohexane:ethyl acetate (2:1 to 1:1)

出典と根拠

ORDレコード
ord-d95121f2ee3e412993db9d86bac97647
出典データセット
uspto-grants-2010_01
特許番号
US07642276B2

反応ノート

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