Beta-Nitrostyrene → (Rac)-3-phenyl-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indol-6-one

HRID 33289

反応式

HRID 33289 の反応式
[N+:1]([CH2:4][CH2:5][C:6]1[C:14]2[C:13]([C:15]([O:17]C)=O)=[CH:12][CH:11]=[CH:10][C:9]=2[NH:8][CH:7]=1)([O-])=O.N1[C:27]2[CH:26]=[CH:25][CH:24]=[C:23](C(OC)=O)[C:22]=2C=C1.[N+](C=CC1C=CC=CC=1)([O-])=O>>[C:22]1([CH:5]2[C:6]3=[CH:7][NH:8][C:9]4[CH:10]=[CH:11][CH:12]=[C:13]([C:14]=43)[C:15](=[O:17])[NH:1][CH2:4]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

4

反応物 3

HCID 7626Beta-NitrostyreneHCID 2733668methyl 1H-indole-4-carboxylateHCID 14916518Methyl 3-(2-Nitroethyl)-1H-indole-4-carboxylate

生成物 1

HCID 10038344(Rac)-3-phenyl-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indol-6-one

反応条件

温度
160 °C

実験手順

In a manner similar to that described for the preparation of methyl 3-(nitroethyl)-indole-4-carboxylate D above, methyl indole-4-carboxylate (85 mg, 0.49 mmol) and nitrostyrene (80 mg, 0.54 mmol) were heated at 160° C. in a sealed tube for 12 h. The product was isolated by silica gel chromatography as a brown oil, 132 mg (83%). The intermediate nitro alkane was reduced/cyclized as described to give (rac)-3-phenyl-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one as a white solid, 51.4 mg (48%, after chromatography and recrystallization). mp 201-203° C.; 1H NMR (300 MHz, d6-DMSO) δ 3.73 (m, 2H), 4.42 (m, 1H), 7.28 (br m, 8H), 7.64 (d, 1H, J=7.9 Hz), 7.77 (d, 1H, J=7.9 Hz), 11.32 (br s, 1H); HRMS (FAB, MH+) Calcd for C17H15N2O: 263.1184, Found: 263.1180; Anal. (C17H14N2O.0.25 H2O) C, H, N.

後処理

  1. customThe product was isolated by silica gel chromatography as a brown oil, 132 mg (83%)
  2. customto give
  3. custom(rac)-3-phenyl-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one as a white solid, 51.4 mg (48%, after chromatography and recrystallization)

出典と根拠

ORDレコード
ord-e92754d7a64149c3b2e5e60bddf0ca59
出典データセット
uspto-grants-2008_09
特許番号
US07429578B2

関連ノート

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