HCID 22627375, compound → HCID 22627429, compound

HRID 278129Notes

Reaction equation

HRID 278129 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([NH2:16])=[O:15])[CH:12]=2)[C:7]([C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])=[C:6]1[CH:22]([OH:25])[CH2:23][CH3:24]>CC(C)=O>[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([NH2:16])=[O:15])[CH:12]=2)[C:7]([C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])=[C:6]1[C:22](=[O:25])[CH2:23][CH3:24]

Participants

3

Reactant 1

HCID 22627375HCID 22627375, compound

Product 1

HCID 22627429HCID 22627429, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-(2-chlorobenzyl)-2-(1-hydroxypropyl)-3-isobutyrylindole-6-carboxamide (19 mg) in acetone (3 ml) was added Jone's reagent until the red color existed continuously. The reaction was quenched by 2-propanol, then the mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give 1-(2-chlorobenzyl)-3-isobutyryl-2-propionylindole-6-carboxamide (9.3 mg).

Workup

  1. customThe reaction was quenched by 2-propanol
  2. additionthe mixture was diluted with ethyl acetate
  3. washwashed with aqueous sodium bicarbonate and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-e1050824983841b98f5d30109edda90e
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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