Sodium Carbonate → HCID 59127378, compound

HRID 1988930Notes

Reaction equation

HRID 1988930 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:6]=[CH:5]2.[CH:18]1([NH:21][C:22]([C:24]2[CH:25]=[C:26]([F:34])[C:27]([CH3:33])=[C:28](B(O)O)[CH:29]=2)=[O:23])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:18]1([NH:21][C:22]([C:24]2[CH:25]=[C:26]([F:34])[C:27]([CH3:33])=[C:28]([C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:6]=[CH:5]4)[CH:29]=2)=[O:23])[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21914527(5-(Cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl)boronic acid2×HCID 22832025tert-Butyl 5-bromo-1H-indazole-1-carboxylate2×

Product 1

HCID 59127378HCID 59127378, compoundYield 211.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of tert-butyl 5-bromo-1H-indazole-1-carboxylate (Intermediate 3) (1.07 g) {5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl}boronic acid (Intermediate 64) (0.85 g) sodium carbonate (1.9 g) and tetrakis(triphenylphosphine)palladium(0) (0.42 g) in 1,2-dimethoxyethane (70 ml) was stirred at reflux under nitrogen for 20 h. the solvent was removed and the residue was partitioned between water (50 ml) and ethyl acetate (50 ml). The aqueous layer was re-extracted with ethyl acetate (3×30 ml) and the combined organic extracts were dried using a hydrophobic filter tube and concentrated under vacuum. The residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (75:25 to 60:40) to give the title compound (3.1 g).

Workup

  1. temperatureat reflux under nitrogen for 20 h. the solvent
  2. customwas removed
  3. customthe residue was partitioned between water (50 ml) and ethyl acetate (50 ml)
  4. extractionThe aqueous layer was re-extracted with ethyl acetate (3×30 ml)
  5. customthe combined organic extracts were dried
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (75:25 to 60:40)

Sources & evidence

ORD record
ord-619e0ebd5a0a4a9584822b60f52bd3a9
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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