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

HRID 1988923노트

반응식

HRID 1988923 반응식
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

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 228320255-Bromo-1H-indazole, N1-BOC protected2회HCID 68676775HCID 68676775, 화합물2회

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d95121f2ee3e412993db9d86bac97647
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642276B2

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