Water → Ethyl 6-bromoisoquinoline-1-carboxylate

反応式

N12CCCN=C1CCCCC2.[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:18](S(C1C=CC=CC=1)(=O)=O)[CH2:17][CH2:16]2.O>C1(C)C=CC=CC=1>[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:18][CH:17]=[CH:16]2

参加物

実験手順

1,8-Diazabicyclo[5.4.0]undec-7-ene (762.3 μL, 5.10 mmol) was added to ethyl 6-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate (1.03 g, 2.43 mmol) in toluene (12 mL) under argon and the reaction was stirred for 18 hours. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:3 ethyl acetate:hexanes to give 400.6 mg (59%) of ethyl 6-bromo-1-isoquinolinecarboxylate as a solid. 1H NMR (400 MHz, d6-DMSO): δ 8.63 (d, J=6 Hz, 1H), 8.43 (d, J=2 Hz, 1H), 8.41 (d, J=10 Hz, 1H), 8.05 (d, J=6 Hz, 1H), 7.91 (dd, J=9, 2 Hz, 1H), 4.46 (q, J=7 Hz, 2H), 1.37 (t, J=7 Hz, 3H). ESI-LCMS m/z 280 (M+H)+.