Triethylamine → HCID 67361188, compound

Participants

Reaction Steps

A mixture of 30 (117 mg, 0.37 mmol), anhydrous DMF (5 mL), Et3N (130 μL, 0.94 mmol), tetrabutylammonium chloride (104 mg, 0.37 mmol), Pd(OAc)2 (9 mg, 40.1 μmol) was stirred for 3 days at room temperature. After removal of the solvent, the residue was diluted with H2O (10 mL), basified with Na2CO3 to pH=10-12 and extracted with CH2Cl2 (3×20 mL). The CH2Cl2 extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography using CH2Cl2/EtOAc (4/1, v/v) as eluent to afford compound 31 (26 mg, yield: 38%); mp 211° C.; IR (KBr) 3099, 3068, 3006, 2913, 2858, 1633, 1517 cm−1; 1H NMR (400 MHz, CDCl3) δ 2.45 (s, 3H), 2.61 (s, 3H), 6.78 (d, 1H, J=7.2 Hz), 6.90 (s, 1H), 7.22 (s, 1H), 7.66 (d, 1H, J=7.2 Hz), 9.55 (brs, 1H); 13C NMR (100 MHz, CDCl3) δ 11.9, 14.3, 101.5, 109.0, 113.3, 113.7, 119.8, 120.6, 131.1, 140.0, 142.6. Anal. Calcd for C11H11N3: C, 71.33; H, 5.99; N, 22.69. Found: C, 70.94; H, 5.89; N, 23.01.

Provenance & Evidence