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Potassium Carbonate → 4'-(2,6-Difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid methyl ester

HRID 220750
Notes
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Reaction equation

HRID 220750 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10](B2OC(C)(C)C(C)(C)O2)=[CH:9][CH:8]=1)=[O:5].[CH3:27][O:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[C:32](Br)[CH:31]=1.C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O>[CH3:27][O:28][C:29]([C:30]1[CH:31]=[C:32]([C:10]2[CH:9]=[CH:8][C:7]([NH:6][C:4](=[O:5])[C:3]3[C:22]([F:26])=[CH:23][CH:24]=[CH:25][C:2]=3[F:1])=[CH:12][CH:11]=2)[C:33]([CH3:36])=[CH:34][CH:35]=1)=[O:38]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 7015747Methyl 3-bromo-4-methylbenzoateHCID 534142112,6-difluoro-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzamide

Product 1

HCID 115526584'-(2,6-Difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid methyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
120 °C

Procedure

A suspension of 2,6-difluoro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (359 mg, 1 mmol), 3-bromo-4-methyl-benzoic acid methyl ester (228 mg, 1 mmol), benzyl(chloro)bis(triphenylphosphine)palladium (38 mg, 0.05 mmol) and K2CO3 (690 mg, 5 mmol) in 1-methylpyrrolidinone (NMP) (5 ml) was degassed with vacuum and heated at 120° C. for 10 hr. After cooling down to room temperature, ethyl acetate (EtOAc) (200 ml) was added and the mixture was washed with water (60 ml×3). The EtOAc was evaporated and the residue was purified by column chromatography on silica gel (Hexanes:EtOAc) to give Compound 1 (286 mg, yield 75%).

Workup

  1. customwas degassed with vacuum
  2. temperatureAfter cooling down to room temperature
  3. additionethyl acetate (EtOAc) (200 ml) was added
  4. washthe mixture was washed with water (60 ml×3)
  5. customThe EtOAc was evaporated
  6. customthe residue was purified by column chromatography on silica gel (Hexanes:EtOAc)

Sources & evidence

ORD record
ord-27f8a9b12d8f40a08952dc67ec86ba31
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202999B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes