Benzyl Bromide → HCID 71150656, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-3-methoxypicolinic acid (140 mg, 0.406 mmol) in DMSO (1.354 mL) were added K2CO3 (67.4 mg, 0.487 mmol) and (bromomethyl)benzene (76 mg, 0.447 mmol). The reaction mixture was heated at 100° C. for 5 min in a Biotage microwave. The reaction mixture was then diluted with H2O and extracted with CH2Cl2. The organic extracts were separated from the aqueous layer in a Biotage phase separator. The organic layer was then concentrated, and the residue was purified by flash chromatography (eluting with 0-50% acetone in hexanes) to afford a white solid (125 mg, 69%): mp 119° C.; 1H NMR (400 MHz, acetone-d6) δ 7.56-7.49 (m, 2H), 7.43-7.27 (m, 5H), 5.98 (s, 2H), 5.40 (s, 2H), 3.97 (d, J=1.1 Hz, 3H), 3.85 (s, 3H), ESIMS m/z 436 ([M+H]+), 434 ([M−H]−).

Provenance & Evidence