Sodium Carbonate → HCID 59843041, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)ethylcarbamate (166 mg, 523 μmol), 2-thiopheneboronic acid (134 mg, 1047 μmol), Na2CO3 (785 μl, 1570 μmol) [2M], and 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (31 mg, 42 μmol) in DME (2 mL) was heated to 85° C. for 45 min. The mixture was partitioned between CH2Cl2 and 10% Na2CO3 and the aqueous was extracted with CH2Cl2 (10 mL). The combined organics were dried over MgSO4 and purified on silica (12 g) eluting with 0>50% of 5% MeOH/CH2Cl2, and isolated as orange crystals from ACN. MS (ESI pos. ion) m/z (MH+): 321 (MH+). Calc'd exact mass for C16H20N2O3S: 320. 1H NMR (400 MHz, Chloroform-d) δ ppm 1.42 (s, 9H) 3.51 (q, J=6.00 Hz, 2H) 4.14 (t, J=5.67 Hz, 2H) 4.96 (br. s., 1H) 6.63 (d, J=9.39 Hz, 1H) 7.01-7.09 (m, 2H) 7.23 (dd, J=4.99, 1.27 Hz, 1H) 7.47-7.51 (m, 1H) 7.61 (dd, J=9.39, 2.54 Hz, 1H).

Provenance & Evidence