Ceric ammonium nitrate → 7-Bromo-3,7B-dihydro-1H-cyclopropa[C]quinolin-2(1AH)-one

To a suspension of 7-bromo-3-(4-methoxybenzyl)-3,7b-dihydro-1H-cyclopropa[c]quinolin-2(1aH)-one (0.300 g, 0.837 mmol) in 9:1 acetonitrile/water (5.5 mL) was added CAN (0.459 g, 0.837 mmol) at room temperature. After stirring at room temperature overnight, the reaction mixture was quenched with water (10 mL) and adjusted pH to 7-9 by using saturated Na2CO3. The resulting mixture was extracted with EtOAc. The combined organic layer was concentrated and purified by flash chromatography (0 to 50% ethyl acetate:hexanes) to afford the title compound (0.18 g, 95% yield) as a pale yellow solid. LCMS, [M+H]+=237.9. 1H NMR (400 MHz, CDCl3) δ 8.15 (s, 1H), 7.24 (d, J=7.7 Hz, 1H), 7.00 (t, J=7.7 Hz, 1H), 6.69 (d, J=7.7 Hz, 1H), 2.84 (td, J=8.1, 5.2 Hz, 1H), 2.22-2.13 (m, 1H), 1.76 (td, J=9.2, 4.7 Hz, 1H), 0.75 (dd, J=10.0, 5.0 Hz, 1H).

1. customthe reaction mixture was quenched with water (10 mL)
2. extractionThe resulting mixture was extracted with EtOAc
3. concentrationThe combined organic layer was concentrated
4. custompurified by flash chromatography (0 to 50% ethyl acetate:hexanes)

ORD record

ord-0509797638ba4123a31a270ca47e1ec8

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062028B2