Diisopropylethylamine → Indole

HRID 249159Notes

Reaction equation

HRID 249159 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
  6. customThe residue was chromatographed on silica gel (50 g)
  7. washeluting with a mixture of ethyl acetate and chloroform (1:20)

Sources & evidence

ORD record
ord-99801fe2c9884714a43dcda710968b72
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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