Sodium Carbonate → HCID 178504705, compound

HRID 1433196Notes

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][S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O)(=[O:26])=[O:25].C(=O)([O-])[O-].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.COCCOC.O>[CH3:23][S:24]([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)(=[O:26])=[O:25]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 5-bromo-2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazole (0.100 g, 0.269 mmol), (2-methylsulfonylphenyl)boronic acid (0.081 g, 0.404 mmol), sodium carbonate (0.228 g, 2.16 mmol), tetrabutylammonium bromide (0.087 g, 0.269 mmol) and 1,1′-[bis(di-tert-butylphosphino)ferrocene]-palladium dichloride (0.035 g, 0.0538 mmol) in DME (2 mL) and H2O (0.5 mL) was heated at 90° C. for 12 hours. The reaction mixture was concentrated under reduced pressure to provide a residue, which was purified by chromatography (silica, hexanes:EtOAc, 1:1) to afford the title compound as an off-white solid. 1H NMR (400 MHz, CD3OD) δ (ppm): 8.19 (dd, 1H, J=7.6 Hz, J=1.2 Hz), 7.76-7.71 (m, 2H), 7.66-7.62 (m, 4H), 7.48 (dd, 1H, J=7.6 Hz, J=1.2 Hz), 7.34 (dd, 1H, J=8.4 Hz, J=1.2 Hz), 7.26 (d, 2H, 8.8 Hz), 5.45 (s, 2H), 2.64 (s, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C24H21F3N3O3S: 488.5 (M+MeCN+H), Found 488.2.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customto provide a residue, which
customwas purified by chromatography (silica, hexanes:EtOAc, 1:1)

Sources & evidence

ORD record: ord-522b80bf296444738604827997cdad75
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612211B2

Reaction notes

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