Water → HCID 86682778, compound

Participants

Reaction Conditions

Reaction Steps

tert-butyl-N-[5-bromo-3-[5-(3-methyl-2-thienyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (750 mg, 1.393 mmol) and tert-butyl 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]sulfonylpiperidine-1-carboxylate (691.5 mg, 1.532 mmol) were suspended in MeCN (7.500 mL)/water (7.500 mL) and Na2CO3 (1.393 mL of 2 M, 2.786 mmol) was added. The reaction mixture was degassed with 3× nitrogen/vacuum cycles. Pd(tBu3P)2 (71.19 mg, 0.1393 mmol) was added and the reaction mixture again degassed 3 times then heated to 65° C. (Dry Syn Temp) for 1.5 hours. The reaction mixture was cooled to ambient temperature and diluted with ethylacetate/water. The aqueous layer was extracted with ethylacetate (×1) and the combined organic extracts washed with brine (×2), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion, 80 g column, eluting with 0 to 30% ethyl acetate/petroleum Ether, (loaded in DCM) to give the sub-title product as a yellow solid (1.01 g, 93% Yield). H NMR (400.0 MHz, DMSO-d6) δ 9.62 (s, 1H), 8.59 (d, 2H), 8.16 (d, 2H), 7.96 (d, 1H), 7.24 (d, 1H), 4.14-3.92 (m, 1H), 3.77 (br d, 1H), 3.44 (br s, 1H), 3.02-2.91 (m, 1H), 2.79 (br t, 1H), 2.67 (s, 3H), 2.05 (br s, 1H), 1.76-1.58 (m, 2H) and 1.35-1.22 (m, 28H) ppm; LC/MS m/z 627 [M−100−56]+.

Provenance & Evidence