Sodium Carbonate → HCID 86621902, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 102A (32 mg, 0.057 mmol) was treated with phenylboronic acid (10 mg, 0.085 mmol), Pd(PPh)4 (6.6 mg, 5.7 μmol), and 2 M Na2CO3 (63 μl, 0.12 mmol) in 1,2-dimethoxyethane (170 μl), heated overnight at 90° C., cooled, diluted with CH2Cl2 (25 mL) and washed with 1 M NaOH (10 mL). The layers were separated and the aqueous was extracted with CH2Cl2 (25 mL). The combined CH2Cl2 layers were dried (MgSO4), filtered, concentrated and purified by chromatography on silica gel eluting with a gradient of 5:1 to 1:2 hexane:EtOAc to provide the title compound. 1H NMR (CDCl3) δ 1.32-1.46 (m, 2H), 1.49 (s, 9H), 1.52-1.82 (m, 3H), 2.15-2.28 (m, 1H), 2.64-2.89 (m, 3H), 3.35 (d, J=10.5 Hz, 1H), 3.54 (t, J=9.2 Hz, 1H), 3.72 (t, J=10.0 Hz, 1H), 3.87 (dd, J=10.7, 5.6 Hz, 1H), 4.00-4.09 (m, 1H), 4.72 (s, 3H), 4.72 (s, 2H), 7.32-7.40 (m, 1H), 7.41-7.50 (m, 3H), 7.61-7.66 (m, 2H), 8.14 (d, J=8.1 Hz, 1H); MS (M+H)+ m/z at 514.

Provenance & Evidence