Reaktion #79335

Reaktionsgleichung

tert-butyl 5-bromo-1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate

2,4-dichlorophenyl boronic acid

Methane

→

title compound

5-(2,4-dichlorophenyl)-1,2,7,8,9,10,11,11a-octahydro-6bH-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole

tert-butyl 5-(2,4-dichlorophenyl)-1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate

Ausbeute 129.5%

Reaktionsbedingungen

Vorschrift

Tert-butyl 5-(2,4-dichlorophenyl)-1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate (510 mg, 65%) was prepared via coupling of tert-butyl 5-bromo-1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate (671 mg, 1.64 mmol) with 2,4-dichlorophenyl boronic acid (470 mg, 2.46 mmol) as illustrated by the general procedure described in Example 534 Step C. 1H NMR (CDCl3, 300 MHz) δ1.48 (s, 9H), 1.81-2.22 (m, 4H), 2.80-3.00 (m, 1H), 3.25 (d, 1H, J=11.5 Hz), 3.31-3.75 (m, 6H), 4.49-4.50 (m, 2H), 6.66 (s, 1H), 6.72 (s, 1H), 7.23 (s, 2H), 7.43 (s, 1H) ppm. CIMS (Methane) m/z=476 [MH]+. The corresponding hydrochloride salt of the title compound was formed from tert-butyl 5-(2,4-dichlorophenyl)-1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate (505 mg) using the procedure described in Example 534 Step D. Then, this salt was free-based using 6 N NaOH, to give the title compound (398 mg, 99%). 1H NMR (CDCl3, 300 MHz) δ1.60-2.30 (m, 5H), 2.70-3.30 (m, 6H), 3.40-3.60 (m, 1H), 3.70-3.80 (m, 1H), 4.30-4.60 (m, 2H), 6.70 (s, 1H), 6.73 (s, 1H), 7.28 (s, 1H), 7.29 (s, 1H), 7.43 (s, 1H) ppm. CIMS (Methane) m/z=376 [MH]+.

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