Diisopropylethylamine → HCID 53859829, compound

HRID 278093Notes

Reaction equation

HRID 278093 reaction equation
Br[CH:2]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=[C:9]([C:19]([O:21][CH3:22])=[O:20])[CH:8]=2)[CH2:3][CH3:4].C(N(CC)C(C)C)(C)C>ClCCCl>[C:14]([C:13]1[C:12]2[C:7](=[CH:8][C:9]([C:19]([O:21][CH3:22])=[O:20])=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH:2]=[CH:3][CH3:4])(=[O:18])[CH:15]([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 22627433HCID 22627433, compound

Product 1

HCID 53859829HCID 53859829, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of methyl 2-(1-bromopropyl)-3-isobutyrylindole-6-carboxylate (179 mg) in 1,2-dichloroethane (8 ml) was added N,N-diisopropylethylamine (0.24 ml) and refluxed for 40 minutes. The resulting mixture was evaporated in vacuo, then the residue was diluted with ethyl acetate and washed with diluted hydrochloric acid, water and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo. Trituration with diethyl ether gave methyl 3-isobutyryl-2-(1-propenyl)indole-6-carboxylate (55.2 mg).

Workup

  1. temperaturerefluxed for 40 minutes
  2. customThe resulting mixture was evaporated in vacuo
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with diluted hydrochloric acid, water and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-72a70c445199461eb3fc8da1cf450800
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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