Diisopropylethylamine → Indole

HRID 1034068Notes

Reaction equation

HRID 1034068 reaction equation
NC1C=C(C=CC=1)C([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=O.C(N(C(C)C)CC)(C)C.C(C1C=CC(C(C2C=CC(CC(C)C)=CC=2)Cl)=CC=1)C(C)C>CN(C)C=O>[NH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 19010817Bis(4-isobutylphenyl)chloromethaneHCID 190247263-(3-Aminobenzoyl)indole

Product 1

HCID 798IndoleYield 210.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-(3-aminobenzoyl)indole (1.2 g) in N,N-dimethylformamide (12 ml) were added diisopropylethylamine (1.77 ml) and a solution of bis(4-isobutylphenyl)chloromethane (1.92 g) in N,N-dimethylformamide (5 ml) at 25° C., and the mixture was allowed to stand at the same temperature for 14 hours. The reaction mixture was partitioned between ethyl acetate and water, and the organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated- The residue was chromatographed on silica gel (50 g) eluting with a mixture of ethyl acetate and chloroform (1:20) to give 3-[3-bis(4-isobutylphenyl)methylamino]benzoyl]indole (1.25 g) as pale yellow amorphous powder.

Workup

  1. customat 25° C.
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated- The residue was chromatographed on silica gel (50 g)
  6. washeluting with a mixture of ethyl acetate and chloroform (1:20)

Sources & evidence

ORD record
ord-6f78c8eed4e34ceabd3ed34d20984f40
Source dataset
uspto-grants-1994_05
Patent number
US05312829

Reaction notes

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