2-Bromo-N,N-dibutyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamide → 3-benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)isophthalate

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis of Intermediate 264I, 3-benzyl 1-methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)isophthalate (1.76 g, 4.62 mmol) and 2-bromo-N,N-dibutyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamide (1.0 g, 2.31 mmol) were converted to the title compound (900 mg, 62%). 1H NMR (CDCl3) δ 8.66 (d, J=1.6 Hz, 1H), 8.23 (dd, J=8.0, 1.6 Hz, 1H), 7.62 (s, 1H), 7.58 (d, J=7.6 Hz, 1H), 7.36-7.32 (m, 3H), 7.25-7.23 (m, 2H), 5.14 (s, 2H), 4.87 (s, 2H), 3.97 (s, 3H), 3.89 (br s, 2H), 3.45 (br s, 2H), 3.34 (t, J=8.0 Hz, 2H), 1.60-1.54 (m, 2H), 1.39-1.21 (m, 6H), 0.95-0.78 (m, 6H), 0.76 (t, J=8.0 Hz, 2H), −0.06 (s, 9H); MS(ESI+) m/z 622.2 (M+H)+.

Provenance & Evidence