1,2-Dichloroethane → 6-tert-butyl 2-methyl 7,8-dihydropyrrolo[3,2-e]indole-2,6(3H)-dicarboxylate

HRID 1183815Notes

Reaction equation

HRID 1183815 reaction equation
N(C(=C[C:10]1C=CC=[C:15]2[C:11]=1[CH:12]=CN2)C(OC)=O)=[N+]=[N-].Br.[C:20]([O:23]CC)(=[O:22])C.[CH:26]1[C:30]2=[C:31]3[C:35]([CH:36]=[CH:37][C:29]2=[N:28][C:27]=1[C:38]([O:40][CH3:41])=[O:39])=[N:34][CH:33]=[CH:32]3.C1C2=C3C(=CC=C2NC1)NC(C(OC)=O)=C3.C(Cl)CCl>CN(C=O)C>[C:11]([O:23][C:20]([N:34]1[C:35]2[C:31](=[C:30]3[C:29](=[CH:37][CH:36]=2)[NH:28][C:27]([C:38]([O:40][CH3:41])=[O:39])=[CH:26]3)[CH2:32][CH2:33]1)=[O:22])([CH3:10])([CH3:12])[CH3:15]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 15480266Methyl 3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylateHCID 18941315HBr ethyl acetateHCID 72253810methyl 2-azido-3-(1H-indol-4-yl)acrylateHCID 178496869HCID 178496869, compound

Product 1

HCID 151147736-tert-butyl 2-methyl 7,8-dihydropyrrolo[3,2-e]indole-2,6(3H)-dicarboxylateYield 47.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

210 mg (0.63 mMol) of 2 was treated with an HBr-ethyl acetate solution for 30 minutes. The solvent was evaporated and the resulting salt 3 was dried under high vacuum. The 0.63 mmol of 3 prepared above was reacted with 210 mg (0.69 mMol) of 4 in 10 mL of DMF in the presence of 133 mg (0.69 mMol) of EDC for 2 hours. The solvent was evaporated and the crude purified over silica. To give 160 mg of 5 (47.6% yield). M+1=518

Workup

  1. customThe solvent was evaporated
  2. dry with materialthe resulting salt 3 was dried under high vacuum
  3. customThe solvent was evaporated
  4. customthe crude purified over silica

Sources & evidence

ORD record
ord-bdce2da070bc44b8afb4249b0e4374c9
Source dataset
uspto-grants-2014_03
Patent number
US08664407B2

Reaction notes

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