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

HRID 1444619Notes

Reaction equation

HRID 1444619 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[C:6]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:5]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]=[CH2:30])C=C.CCN(CC)CC>C(Cl)Cl>[CH:17]1([C:6]2[C:7]3[CH:8]=[CH:9][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:12]=3[N:4]3[CH2:1][CH:30]=[CH:29][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[C:5]=23)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 58765270methyl 1-allyl-3-cyclohexyl-2-(2-vinylphenyl)1H-indole-6-carboxylate

Product 1

HCID 11667856methyl 13-cyclohexyl-7H-indolo[2,1-a][2]benzazepine-10-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude methyl 1-allyl-3-cyclohexyl-2-(2-vinylphenyl)1H-indole-6-carboxylate was dissolved in DCM (0.02M) and treated with Zhan catalyst I (0.3 eq) at 35° C. for 1 h. NEt3 (7 eq) were added and the solvent was removed in vacuo. The residue was purified by chromatography (PE/EtOAc 95:5) to afford the title compound (84%); MS (ES+) m/z 372 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by chromatography (PE/EtOAc 95:5)

Sources & evidence

ORD record
ord-ca16578ddb8047349ba56253d72f05d2
Source dataset
uspto-grants-2010_02
Patent number
US07662809B2

Reaction notes

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