Methane → Tert-butyl 5-(3,4,5-trimethoxyphenyl)-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 51054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51054
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.[CH3:26][O:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35].C>>[CH3:37][O:36][C:32]1[CH:31]=[C:30]([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]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:17][CH2:18][CH:5]34)[CH:10]=2)[CH:29]=[C:28]([O:27][CH3:26])[C:33]=1[O:34][CH3:35]

Komponenten

4

Edukt 3

HCID 297MethaneHCID 27343903,4,5-Trimethoxybenzeneboronic 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 1

HCID 22735406Tert-butyl 5-(3,4,5-trimethoxyphenyl)-1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylateAusbeute 75 %

Versuchsvorschrift

Tert-butyl 5-(3,4,5-trimethoxyphenyl)-1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole-9-carboxylate (609 mg, 75%) was prepared via coupling of the 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 3,4,5-trimethoxyphenyl boronic acid (522 mg, 2.46 mmol) as illustrated above using the typical procedure for Suzuki coupling. 1H NMR (CDCl3, 300 MHz) δ1.49 (s, 9H), 1.80-2.20 (m, 4H), 2.80-2.91 (m, 1H), 3.25 (d, 1H, J=10.8 Hz), 3.42-3.70 (m, 1H), 3.83 (s, 3H), 3.88 (s, 6H), 4.40-4.51 (m, 2H), 6.69 (s, 2H), 6.82 (s, 1H), 6.86 (s, 1H) ppm. CIMS (Methane) m/z=497 [MH]+.

Quellen und Nachweise

ORD-Eintrag
ord-487319e4ec2d4b398d8d4af648041547
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713471B1

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