Ethyl diazoacetate → HCID 90460711, compound

HRID 588890Notes

Reaction equation

HRID 588890 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[CH:5]2.[N+](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N-]>C(Cl)Cl.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+2]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 104877765,6-dichloro-1H-indole

Product 1

HCID 90460711HCID 90460711, compoundYield 8.2%

Reagents, catalysts & solvents 2

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5,6-dichloro-1H-indole (1.0 g, 5.37 mmol), Cu(OTf)2 (194 mg, 0.537 mmol) in DCM (15 mL) at RT, ethyl 2-diazoacetate (918 mg, 8.05 mmol) was added dropwise. The resulting mixture was stirred at RT for 16 h, quenched with water, and then extracted dichloromethane. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by Prep-HPLC to afford the desired product (120 mg, 8.2% yield) as light yellow solid. ESI-MS m/z: 272.1[M+H]+.

Workup

  1. customquenched with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-c5396f372b9e450bb668e57b1ee9d9f7
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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