Sodium Carbonate → HCID 178527415, compound

HRID 1433202Notes

Reaction equation

C(OC([N:8]1[C:12]2[CH:13]=[CH:14][C:15](B3OC(C)(C)C(C)(C)O3)=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=1)=O)(C)(C)C.Br[CH2:39][CH:40]([S:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)(=[O:44])=[O:43])O.C(=O)([O-])[O-:52].[Na+].[Na+]>COCCOC.O>[F:37][C:34]([F:35])([F:36])[C:31]1[CH:32]=[CH:33][C:28]([O:27][CH2:26][C:9]2[NH:8][C:12]3[CH:13]=[CH:14][C:15]([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=4[S:42]([CH2:40][CH2:39][OH:52])(=[O:44])=[O:43])=[CH:16][C:11]=3[N:10]=2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-(4-trifluoromethyl-phenoxymethyl)-benzoimidazole-1-carboxylic acid tert-butyl ester (0.046 g, 0.0887 mmol), 2-bromophenylsulfonylethanol (0.036 g, 0.133 mmol), sodium carbonate (0.056 g, 0.532 mmol), and 1,1′-[bis(di-tert-butylphosphino)ferrocene]-palladium dichloride (0.006 g, 0.00887 mmol) in DME (2 mL) and H2O (0.5 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, EtOAc) to afford the title compound as a light brown solid (0.025 g, 59%). 1H NMR (400 MHz, CD3OD) δ (ppm): 8.17 (dd, 1H, J=8.0 Hz, J=1.2 Hz), 7.76-7.61 (m, 6H), 7.46 (dd, 1H, J=7.6 Hz, J=1.2 Hz), 7.34 (d, 1H, J=7.6 Hz), 7.26 (d, 2H, J=8.8 Hz), 5.46 (s, 2H), 3.63 (t, 2H, J=6.6 Hz), 2.91 (t, 2H, J=12.8 Hz). Mass Spectrum (LCMS, ESI pos.) Calcd. For C25H23F3N3O4S: 518.5 (M+MeCN+H), Found 518.2.

Workup

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

Sources & evidence

ORD record: ord-86947884781444c7b30baa29cafc4579
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612211B2

Reaction notes

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