Sodium Carbonate → HCID 178497613, compound

HRID 1433218Notes

Reaction equation

Br[C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7]([CH2:9][O:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)=[N:8][C:4]=2[CH:3]=1.[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O)=[O:26].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[CH3:23][O:24][C:25](=[O:26])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7]([CH2:9][O:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)=[N:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-bromo-2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazole (0.500 g, 1.35 mmol), (2-methoxycarbonylphenyl)boronic acid (0.290 g, 1.62 mmol), sodium carbonate (0.857 g, 8.10 mmol), and 1,1′-[bis(di-tert-butylphosphino)ferrocene]-palladium dichloride (0.088 g, 0.135 mmol) in DME (10 mL) and H2O (2.5 mL) was heated at 80° C. for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by chromatography (silica, hexanes: EtOAc, 1:1) to afford the product as a yellow oil (0.494 g, 86%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by chromatography (silica, hexanes: EtOAc, 1:1)

Sources & evidence

ORD record: ord-5ff8f947d99c49babf04932088b5983a
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612211B2

Reaction notes

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