1-(chloromethyl)-3-[(5-methoxyindol-2-yl)carbonyl]-5-nitro-1,2-dihydro-3H-benz[e]indole → [5-amino-1-(chloromethyl)-1,2-dihydrobenzo[e]indol-3-yl]-(5-methoxy-1H-indol-2-yl)methanone
Reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([N+:16]([O-])=O)=[CH:7][C:6]=2[N:5]([C:19]([C:21]2[NH:22][C:23]3[C:28]([CH:29]=2)=[CH:27][C:26]([O:30][CH3:31])=[CH:25][CH:24]=3)=[O:20])[CH2:4]1>C1COCC1.O=[Pt]=O>[NH2:16][C:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[C:11]2[CH:3]([CH2:2][Cl:1])[CH2:4][N:5]([C:19]([C:21]3[NH:22][C:23]4[C:28]([CH:29]=3)=[CH:27][C:26]([O:30][CH3:31])=[CH:25][CH:24]=4)=[O:20])[C:6]=2[CH:7]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 14d (140 mg, 0.32 mmol) in THF (10 mL) was hydrogenated over PtO2 at 50 psi for 2 h. After removal of the catalyst, the solution was concentrated to a small volume below 25° C. and diluted with iPr2O to give 15d (124 mg, 95%), mp 250-255° C. 1H NMR [(CD3)2SO] δ 11.56 (d, J=1.6 Hz, 1 H, NH), 8.08 (d, J=8.4 Hz, 1 H, H-6), 7.76 (d, J=8.2 Hz, 1 H, H-9), 7.70 (s, 1 H, H-4), 7.46 (t, J=7.6 Hz, 1 H, H-8), 7.40 (d, J=8.8 Hz, 1 H, H-7'), 7.28 (t, J=7.6 Hz, 1 H, H-7), 7.16 (d, J=2.4 Hz, 1 H, H-4'), 7.08 (d, J=1.8 Hz, 1 H, H-3'), 6.91 (dd, J=8.8, 2.5 Hz, 1 H, H-6'), 5.98 (s, 2 H, NH2), 4.73 (dd, J=10.8, 8.9 Hz, 1 H, H-2), 4.51 (dd, J=10.9, 1.7 Hz, 1 H, H-2), 4.17-4.08 (m, 1 H, H-1), 3.98 (dd, J=11.0, 3.1 Hz, 1 H, CHHCl), 3.78 (s, 3 H, OCH3), 3.75 (dd, J=11.0, 8.1 Hz, 1 H, CHHCl).
Workup
- customAfter removal of the catalyst
- concentrationthe solution was concentrated to a small volume below 25° C.
- additiondiluted with iPr2O
Sources & evidence
- ORD record
- ord-6e8b609dedeb42118c1e3b15b6be0892
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06130237
Reaction notes
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