反应详情

A solution of 2-bromo-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]benzamide (0.30 g, 0.84 mmole), pyridine-4-boronic acid (0.20 g, 1.63 mmole), tetrakis(triphenylphosphine)palladium(0) (29 mg, 0.025 mmole), and Cs2CO3 (1.10 g, 3.38 mmole) in 10:1 DME/H2O (25 mL) was degassed, then was heated under N2 overnight. The resulting mixture was concentrated in vacuo, and the residue was taken up in 10% NaOH solution. The mixture was extracted with CH2Cl2, and the combined organic extracts were washed with brine and dried (MgSO4). Flash chromatography on silica gel (3% MeOH/CH2Cl2) followed by preparative TLC (3% MeOH/CH2Cl2) gave the title compound (98 mg, 33%) as a white solid: 1H NMR (300 MHz, CDCl3) indicated an approximately 5:1 mixture of amide rotamers; for the major rotamer: 6 8.50-8.65 (m, 2H), 7.00-7.60 (m, 10H), 6.27 (s, 1H), 4.50-5.00 (m, 2H), 3.62 (s, 3H), 2.49 (s, 3H); for the minor rotamer: δ 8.65-8.75 (m, 2H), 7.00-7.60 (m, 10H), 6.12 (s, 1H), 4.50-5.00 (m, 2H), 3.41 (s, 3H), 2.86 (s, 3H); MS (ES) m/e 356 (M+H)+. Anal. Calcd for C23H21N3O.0.10H2O: C, 77.33; H, 5.98; N, 11.76. Found: C, 77.07; H, 5.98; N, 11.56.

1. temperaturewas heated under N2 overnight
2. concentrationThe resulting mixture was concentrated in vacuo
3. extractionThe mixture was extracted with CH2Cl2
4. washthe combined organic extracts were washed with brine
5. dry with materialdried (MgSO4)