Sodium Carbonate → HCID 11990754, compound

HRID 271115Notes

Reaction equation

HRID 271115 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=2)([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:3]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1B(O)O.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>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:15]2[CH:16]=[C:17]([C:27]3[CH:28]=[C:23]([F:22])[CH:24]=[CH:25][C:26]=3[F:29])[CH:18]=[CH:19][CH:20]=2)([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 15951414HCID 15951414, compound

Product 1

HCID 11990754HCID 11990754, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2-amino-5-(3-bromophenyl)-3-methyl-5-pyridin-4-yl-3,5-dihydro-4H-imidazol-4-one (104 mg, 0.3 mmol) in DME (5 mL) is added 2,5-difluorophenylboronic acid (96 mg, 0.6 mmol), tetrakis(triphenylphosphine)palladium (35 mg, 0.03 mmo) and 2.0M aqueous sodium carbonate (0.6 mL, 1.2 mmol) at room temperature. The reaction mixture is refluxed for 1 hour and cooled. After evaporation of the solvent, the crude mixture is purified by chromatography (silica gel, EtOAc/2M methanolic NH3: 92/8) to give the title compound (95 mg, 84%) as a solid. mp: 200-202° C.; MS(+) ES: 379 (M+H)+.

Workup

  1. temperatureThe reaction mixture is refluxed for 1 hour
  2. temperaturecooled
  3. customAfter evaporation of the solvent
  4. customthe crude mixture is purified by chromatography (silica gel, EtOAc/2M methanolic NH3: 92/8)

Sources & evidence

ORD record
ord-b139573ecabe42ad82185040443801b4
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Reaction notes

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