Indole → HCID 66920309, compound

HRID 1510072Notes

Reaction equation

HRID 1510072 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15]1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[CH3:13][O:12][CH2:11][CH2:10][CH2:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15]1

Participants

7

Reactant 4

HCID 798IndoleHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 58488432HCID 58488432, compound

Product 1

HCID 66920309HCID 66920309, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of the compound of step 1 (8.00 g, 27.4 mmol), indole (3.21 g, 27.4 mmol), copper(I) iodide (522 mg, 2.74 mmol), L-proline (636 mg, 5.48 mmol) and potassium carbonate (7.68 g, 54.8 mmol) in DMSO (50 ml) was stirred for 26 h at 125° C. The mixture was quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered and evaporated. The residue was purified by preparative HPLC. The eluate was lyophilized overnight to give 3.10 g of the title compound.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EA
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by preparative HPLC
  8. waitThe eluate was lyophilized overnight

Sources & evidence

ORD record
ord-661fa915bfdc4959bf88256deb5011b7
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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