methyl 13-cyclohexyl-7H-indolo[2,1-a][2]benzazepine-10-carboxylate → methyl 13-cyclohexyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

HRID 1394843Notes

Reaction equation

HRID 1394843 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:25]([O:27][CH3:28])=[O:26])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]=[CH:18][C:17]4[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C.C(OCC)(=O)C>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:25]([O:27][CH3:28])=[O:26])=[CH:12][C:13]=3[N:14]3[CH2:20][CH2:19][CH2:18][C:17]4[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 11667856methyl 13-cyclohexyl-7H-indolo[2,1-a][2]benzazepine-10-carboxylate

Product 1

HCID 11624952methyl 13-cyclohexyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylateYield 100.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Method A: Palladium on carbon (60 mg of 10%) was added to a solution of Example 1 (60 mg, 0.16 mmol) in 60 mL of ethanol and 10 mL of ethyl acetate. The reaction vessel was flushed with H2. The resulting mixture was stirred at room temperature under an atmosphere of hydrogen (balloon pressure) for 4 hours. The mixture was filtered and concentrated to provide the desired product (60 mg, 100% yield) as a colorless solid. ESI-MS m/z 373 (MH+); 1H NMR (500 MHz, CDCl3) δ 1.22 (m, 1H), 1.39 (m, 2H), 1.65 (m, J=12.51 Hz, 1H), 1.76 (d, J=8.85 Hz, 2H), 1.91 (d, J=11.90 Hz, 1H), 1.91 (d, J=11.90 Hz, 1H), 2.06 (m, 3H), 2.38 (m, 1H), 2.56 (m, 1H), 2.68 (dd, J=13.43, 6.71 Hz, 1H), 2.91 (m, 1H), 3.70 (m, 1H), 3.97 (m, 3H), 4.43 (dd, J=14.34, 6.71 Hz, 1H), 7.35 (m, 4H), 7.73 (dd, J=8.54, 1.53 Hz, 1H), 7.87 (d, J=8.54 Hz, 1H), 8.08 (s, 1H).

Workup

  1. customThe reaction vessel was flushed with H2
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b58b9d8d7ef74485b9b41e22d9900bad
Source dataset
uspto-grants-2008_03
Patent number
US07348425B2

Reaction notes

Loading…