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

HRID 51055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51055
Br[C:2]1[CH:3]=[C:4]2[C:8]3=[C:9]([O:11][CH2:12][CH2:13][N:7]3[CH:6]3[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18][CH:5]23)[CH:10]=1.[C:26]1(B(O)O)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1>>[CH4:2].[C:26]1([C:2]2[CH:3]=[C:4]3[C:8]4=[C:9]([O:11][CH2:12][CH2:13][N:7]4[CH:6]4[CH2:14][CH2:15][NH:16][CH2:17][CH2:18][CH:5]34)[CH:10]=2)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1.[C:34]1([C:2]2[CH:3]=[C:4]3[C:8]4=[C:9]([O:11][CH2:12][CH2:13][N:7]4[CH:6]4[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:17][CH2:18][CH:5]34)[CH:10]=2)[C:35]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][CH:33]=1

Komponenten

5

Edukt 2

HCID 2545321-Naphthaleneboronic acidHCID 22735371tert-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

Produkt 3

HCID 297MethaneHCID 22735516tert-butyl 5-(1-naphthyl)-1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylateAusbeute 268,4 %HCID 227359495-(1-naphthyl)-1,2,7,8,9,10,11,11a-octahydro-6bH-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole

Versuchsvorschrift

Tert-butyl 5-(1-naphthyl)-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, 90%) 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 1-naphthyl boronic acid (423 mg, 2.46 mmol) as illustrated by the general procedure described in Example 534 Step C. CIMS (Methane) m/z=457 [MH]+ The corresponding hydrochloride salt of the title compound was formed from tert-butyl 5-(1-naphthyl)-1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate (670 mg) using the procedure described in Example 534 Step C. Then, this salt was free-based using 6 N NaOH, to give the title compound (527 mg, 99%). 1H NMR (CDCl3, 300 MHz) δ1.80-2.40 (m, 5H), 2.80-3.00 (m, 3H), 3.00-3.15 (m, 1H), 3.40-3.60 (m, 1H), 3.62-3.86 (m, 1H), 4.28-4.62 (m, 4H), 6.77 (s, 2H), 7.30-7.60 (m, 4H), 7.75 (d, 1H, J=8.1 Hz), 7.85 (d, 1H, J=8.0 Hz), 8.04 (d, 1H, J=8.1 Hz) ppm. CIMS (Methane) m/z=357 [MH]+.

Quellen und Nachweise

ORD-Eintrag
ord-b71035b8b0ad4a1b84715de762c0b7cc
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713471B1

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