Benzonitrile, 4-bromo- → HCID 178461986, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-methyl-2-((S)-1-(2-(trifluoromethyl)phenyl)ethylamino)thiazol-4(5H)-one (0.2000 g, 0.662 mmol), 4-bromobenzonitrile (0.301 g, 1.65 mmol), Pd2(dba)3 (0.0303 g, 0.0331 mmol), (S)-2-(diphenylphosphino)-1-(2-(diphenylphosphino)-naphthalen-1-yl)naphthalene (0.0618 g, 0.0992 mmol), and LiN(TMS)2 (0.277 g, 1.65 mmol) was added toluene (8 mL) in a glove box. The mixture was gradually heated to 95° C. and stirred overnight. The reaction was quenched with NH4Cl (5 mL), and the reaction mixture was extracted three times with ethylacetate (30 mL). The organic phase was dried over Na2SO4, filtered and concentrated under vacuum. The crude was purified by chromatography on silica gel using 22% ethylacetate/hexane to remove the impurities and then 36% ethylacetate/hexane to obtain the product as a light yellow solid. MS (ESI, pos. ion) m/z: 404 (M+1), 402 (M-1). 1H NMR (CDCl3, 400 MHz): δ1.71-1.78 (m, 3H), 1.98-2.09 (m, 3H), 5.05 (q, J=8 Hz, 1H), 7.39-7.68 (m, 7H), 7.84 (d, J=8 Hz, 1H), 10.97 (s, 1H). % de (by 1H NMR): 48%.

Provenance & Evidence