Methanol → HCID 66869085, compound

HRID 729996

Reaction equation

HRID 729996 reaction equation
[CH2:1]([N:8]1[C:12](Br)=[CH:11][N:10]=[C:9]1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].CO>CC([O-])=O.CC([O-])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd+2].COCCOC>[CH2:1]([N:8]1[C:12]([C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][C:20]=2[F:22])=[CH:11][N:10]=[C:9]1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 668687951-Benzyl-2-methyl-5-bromo-1H-imidazole

Product 1

HCID 66869085HCID 66869085, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 84538Palladium(2+) acetate--triphenylphosphane (1/2/2)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Heat a mixture of 1-benzyl-2-methyl-5-bromo-1H-imidazole (4.71 g, 18.7 mmol), 2,4-difluorophenyl boronic acid (6.92 g, 43.8 mmol), bis(acetato)bis(triphenylphosphine)-palladium(II) (1.4 g, 1.875 mmol), 2N Na2CO3 (19 mL, 38 mmol), MeOH (19 mL) and 1,2-dimethoxyethane (120 mL) to reflux for 18 h. Cool to RT. Add water and EtOAc and separate the layers. Dry organic layer over MgSO4, filter, and concentrate. Purify the residue (silica gel chromatography, eluting with EtOAc:CH2Cl2 mixtures) to give the desired compound (3.59 g).

Workup

  1. temperatureHeat
  2. temperatureto reflux for 18 h
  3. customAdd water and EtOAc and separate the layers
  4. filtrationDry organic layer over MgSO4, filter
  5. concentrationconcentrate
  6. customPurify
  7. washthe residue (silica gel chromatography, eluting with EtOAc:CH2Cl2 mixtures)

Sources & evidence

ORD record
ord-663562bcc74b4a6da309af86daf84192
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Linked notes

Loading…