Hydrochloric Acid → N-cyclopropyl-3-(1H-indazol-6-yl)-4-methylbenzamide

HRID 1988936Notes

Reaction equation

HRID 1988936 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10](Br)[CH:11]=2)[CH:6]=[N:5]1)(=O)C.[CH:14]1([CH2:17][NH:18][C:19](=[O:35])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22](B3OC(C)(C)C(C)(C)O3)[CH:21]=2)[CH2:16]C1.[C:36](=O)([O-])[O-].[Na+].[Na+].Cl>COCCOC>[CH:17]1([NH:18][C:19](=[O:35])[C:20]2[CH:21]=[CH:22][C:23]([CH3:36])=[C:24]([C:10]3[CH:11]=[C:12]4[C:7]([CH:6]=[N:5][NH:4]4)=[CH:8][CH:9]=3)[CH:25]=2)[CH2:14][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium Carbonate2×HCID 569728871-(6-bromo-1H-indazol-1-yl)ethanone2×HCID 68676775HCID 68676775, compound2×

Product 1

HCID 59127383N-cyclopropyl-3-(1H-indazol-6-yl)-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 1-acetyl-6-bromo-1H-indazole (Intermediate 65) (0.50 g) N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 5) (0.59 g) aqueous sodium carbonate (1M, 2.35 ml) and PdCl2dppf (0.237 g) in 1,2-dimethoxyethane (30 ml) was stirred at reflux under nitrogen for 16 h. More sodium carbonate (2.3 ml) and catalyst (120 mg) were added and reflux was continued for a further 4 h. Conc. hydrochloric acid (1 ml) was added and the mixture was heated for a further 1 h. The mixture was absorbed onto silica then purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (2:1 to 1:4) to give the title compound (0.25 g).

Workup

  1. temperatureat reflux under nitrogen for 16 h
  2. temperaturereflux
  3. temperaturethe mixture was heated for a further 1 h
  4. customThe mixture was absorbed onto silica
  5. customthen purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (2:1 to 1:4)

Sources & evidence

ORD record
ord-71f47cfd2bf14bbfa54d5f5706abbf14
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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