Stannous chloride dihydrate → (S)-4-(2-(2-(4-amino-1,3-dioxoisoindolin-2-yl)acetoxy)-2-(3-(cyclopropylmethoxy)-4 (difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide

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Reaction Steps

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(5-nitro-1,3-dioxoisoindolin-2-yl)acetoxy)ethyl)pyridine 1-oxide (80 mg, 0.123 mmol) was dissolved in THF (10 ml), and added with tin(II) chloride dihydrate (80.0 mg, 0.355 mmol). The reaction was stirred at RT for 3 days. The reaction was quenched by addition of K2CO3/H2O (15% w/w; 50 ml). The solid precipitated was filtered on paper, and the solution extracted with EtOAc (50 ml). The organic phase was washed with K2CO3/H2O conc. (×3), dried over Na2SO4 and the solvent removed to yield the titled compound (50.0 mg) as yellow oil (yield=66%). 1H NMR (400 MHz, acetone) ppm 8.20 (s, 2H), 7.50 (d, J=7.50 Hz, 1H), 7.14-7.24 (m, 2H), 7.01-7.13 (m, 3H), 6.92 (t, J=75.00 Hz, 1H), 6.17 (dd, J=9.48, 5.07 Hz, 3H), 4.37 (d, J=7.50 Hz, 2H), 4.00 (dd, J=7.06, 3.09 Hz, 2H), 3.53 (m, 1H), 3.34 (d, J=4.41 Hz, 1H), 1.30 (br. s., 2H), 0.56-0.68 (m, 2H), 0.41 (d, J=4.41 Hz, 2H). MS/ESI+ [MH]+=608.39.

Provenance & Evidence