4-Methoxy-beta-nitrostyrene → (Rac)-3-(4-methoxyphenyl)-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indol-6-one

HRID 33346Notes

Reaction equation

HRID 33346 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12]C)=O)[C:4]=2[CH:3]=[CH:2]1.[CH3:14][O:15][C:16]1[CH:26]=[CH:25][C:19]([CH:20]=[CH:21][N+:22]([O-])=O)=[CH:18][CH:17]=1>>[CH3:14][O:15][C:16]1[CH:26]=[CH:25][C:19]([CH:20]2[C:3]3=[CH:2][NH:1][C:9]4[CH:8]=[CH:7][CH:6]=[C:5]([C:4]=43)[C:10](=[O:12])[NH:22][CH2:21]2)=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 2298434-Methoxy-beta-nitrostyreneHCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 22266665(Rac)-3-(4-methoxyphenyl)-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indol-6-one

Procedure

In a manner similar to that described for the preparation of Example Q, methyl indole-4-carboxylate and p-methoxy nitrostyrene were condensed and the resulting nitro alkane was reduced/cyclized to give, after recrystallization (CH2Cl2/MeOH/hexanes), (rac)-3-(4-methoxyphenyl)-3,4,5,6-tetrahydro-1H-axepino[5,4,3-cd]indol-6-one, 16.9 mh (50%) as a white solid: m.p. 221-223° C.; 1H NMR (300 MHz, d4—MeOH) δ 3.57 (br m, 5H), 5.15 (br s, 1H) 6.62 (m, 2H), 6.86 (m, 2H), 7.08 (app t, J=7.8 Hz, 1H), 7.11 (s, 1H), 7.37 (d, J=7.9 Hz, 1H), 7.73 (d, J=7.5 Hz, 1H). Anal. (C19H16N2O20.25 H2O) C, H, N.

Workup

  1. customcondensed
  2. customto give
  3. customafter recrystallization (CH2Cl2/MeOH/hexanes), (rac)-3-(4-methoxyphenyl)-3,4,5,6-tetrahydro-1H-axepino[5,4,3-cd]indol-6-one, 16.9 mh (50%) as a white solid

Sources & evidence

ORD record
ord-429cdb35cbd2454d8c006eef32cae810
Source dataset
uspto-grants-2008_09
Patent number
US07429578B2

Reaction notes

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