methyl 4-allyl-6-cyclohexyl-5-(2-vinylphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate → Methyl 12-cyclohexyl-7H-thieno[2',3':4,5]pyrrolo[2,1-a][2]benzazepine-10-carboxylate

HRID 1008978Notes

Reaction equation

HRID 1008978 reaction equation
[CH2:1]([N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2C=C)=[C:7]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:6]2[S:23][C:24]([C:26]([O:28][CH3:29])=[O:27])=[CH:25][C:5]1=2)[CH:2]=[CH2:3]>C(Cl)Cl.Cl[Ru](Cl)(=CC1C=C(Cl)C=CC=1OC(C)C)=C1N(C2C(C)=CC(C)=CC=2C)C=CN1C1C(C)=CC(C)=CC=1C>[CH:17]1([C:7]2[C:6]3[S:23][C:24]([C:26]([O:28][CH3:29])=[O:27])=[CH:25][C:5]=3[N:4]3[CH2:1][CH:2]=[CH:3][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[C:8]=23)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

4

Reactant 1

HCID 67298543methyl 4-allyl-6-cyclohexyl-5-(2-vinylphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 67298526Methyl 12-cyclohexyl-7H-thieno[2',3':4,5]pyrrolo[2,1-a][2]benzazepine-10-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 86629781dichloro(5-chloro-2-isopropoxybenzylidene)(1,3-dimesityl-1,3-dihydro-2H-imidazol-2-ylidene)rutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl 4-allyl-6-cyclohexyl-5-(2-vinylphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate was dissolved in DCM (0.02M) and treated with Zhan catalyst (dichloro(5-chloro-2-isopropoxybenzylidene)(1,3-dimesityl-1,3-dihydro-2H-imidazol-2-ylidene)ruthenium; RC-301; 0.3 eq.) at 35° C. for 2 h. After removal of the solvent the residue was purified by chromatography (PE/EtOAc 14:1) to afford the title compound in 83% yield. 1H-NMR (400 MHz, CDCl3, 300 K, δ) 7.74 (s, 1H), 7.57-7.56 (m, 1H), 7.45-7.35 (m, 3H), 6.82 (d, 1H, J 10.4), 6.30-6.25 (m, 1H), 4.47 (bs, 2Hs), 3.93 (s, 3H), 2.83-2.76 (m, 1H), 1.85-1.29 (m, 10H); MS (ES+) m/z 378 (M+H)+.

Workup

  1. customAfter removal of the solvent the residue
  2. customwas purified by chromatography (PE/EtOAc 14:1)

Sources & evidence

ORD record
ord-15036802791a4d318a7ecf2a31dd2f9f
Source dataset
uspto-grants-2011_07
Patent number
US07973026B2

Reaction notes

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