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

HRID 1988923Notes

Reaction equation

HRID 1988923 reaction equation
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

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 22832025tert-Butyl 5-bromo-1H-indazole-1-carboxylate2×HCID 68676775HCID 68676775, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-d95121f2ee3e412993db9d86bac97647
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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