Sodium Carbonate → Methyl 6-amino-2-(3-(tert-butoxycarbonyl)phenyl)nicotinate

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Reaction Conditions

Reaction Steps

To a flask containing methyl 6-amino-2-chloronicotinate (300 mg, 1.6 mmol), 3-(tert-butoxycarbonyl)phenylboronic acid (540 mg, 2.4 mmol) and Pd(PPh3)4 (90 mg, 0.080 mmol) was added DME (16 mL) and saturated Na2CO3 aqueous solution (1.6 mL). The flask was flushed with N2 (g) and heated at 80° C. under N2 atmosphere overnight. The solution was filtered and concentrated. The residue was purified by column chromatography (0-50% ethyl acetate—hexanes) to yield methyl 6-amino-2-(3-(tert-butoxycarbonyl)phenyl)nicotinate as a white solid (450 mg, 85%). ESI-MS m/z calc. 328.1, found 329.3 (M+1)+. Retention time 1.19 minutes. 1H NMR (400 MHz, DMSO-d6) δ 7.91-7.86 (m, 3H), 7.59-7.57 (m, 1H), 7.49 (t, J=7.6 Hz, 1H), 6.86 (s, 2H), 6.48 (d, J=8.7 Hz, 1H), 3.54 (s, 3H), 1.56 (s, 9 H).

Provenance & Evidence