2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → HCID 59375069, compound

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Reaction Steps

Using the procedure of Example 3-2, benzyl 5-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazol-2-ylcarbamate (Intermediate 50-4(a), 300 mg, 0.678 mmol) and 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (Intermediate 50-1, 237 mg, 1.017 mmol) were converted into benzyl 5-(3-amino-2-methylphenyl)-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazol-2-ylcarbamate, TFA salt, isolated as a white solid after preparative HPLC purification (60 mg, 15%). 1H NMR (400 MHz, methanol-d4) δ 7.63 (1 H, dd, J=7.7, 2.9 Hz), 7.18-7.46 (8 H, m), 6.82 (1H, dd, J=7.5, 2.8 Hz), 5.10 (2 H, s), 3.90 (1 H, br. s.), 3.14 (1 H, d, J=4.8 Hz), 2.72 (1H, br. s.), 1.77-2.19 (6 H, m), 1.51-1.68 (1 H, m). Mass spectrum m/z 469.3 (M+H)+.

Provenance & Evidence