Trifluoroacetic acid → 3-(4-Amino-3-methoxyphenyl)-7-iodofuro[3,2-c]pyridin-4-amine

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Reaction Steps

Tert-butyl 4-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2-methoxyphenylcarbamate (3.98 g, 8.28 mmol) was added to a 20% solution of trifluoroacetic acid in dichloro-methane (150 mL). The mixture was stirred for two hours and then the solvent was removed in vacuo. To the residue was added water (15 mL) and dichloromethane (25 mL). The mixture was adjusted to pH 12 with 1 N aqueous sodium hydroxide and the layers were separated. The aqueous layer was extracted with dichloromethane (2×10 mL) and the combined organic layers were dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give the title compound (2.534 g, 80%). 1H NMR (DMSO-d6, 400 MHz) □ 8.03 (s, 1H), 7.94 (s, 1H), 6.91 (d, 1H), 6.82 (dd, 1H), 6.75 (d, 1H), 5.69–5.77 (bs, 2H), 4.96–5.05(bs, 2H), 3.81 (s, 3H); RP-HPLC (Conditions f) Rt 11.22 min.; MS: MH+ 382.

Provenance & Evidence