Triethylamine → 1-(1-Acetyl-6-benzyloxy-3-methyl-1H-indol-5-yl)-2-bromo-ethanone

HRID 1433161Notes

Reaction equation

HRID 1433161 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:21](=[O:25])[CH:22](Br)[Br:23])=[C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=2)[C:6]([CH3:26])=[CH:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.P(OCC)(OCC)=O>C1COCC1.CCOC(C)=O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:21](=[O:25])[CH2:22][Br:23])=[C:10]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:11]=2)[C:6]([CH3:26])=[CH:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 579348261-(1-acetyl-6-benzyloxy-3-methyl-1H-indol-5-yl)-2,2-dibromo-ethanoneHCID 178476833HCID 178476833, compound

Product 1

HCID 579348421-(1-Acetyl-6-benzyloxy-3-methyl-1H-indol-5-yl)-2-bromo-ethanoneYield 11.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude product 1-(1-acetyl-6-benzyloxy-3-methyl-1H-indol-5-yl)-2,2-dibromo-ethanone (0.42 g, 0.88 mmol) was suspended in THF (4 ml), followed by the addition of triethylamine (0.12 ml, 0.89 mmol) and (EtO)2P(O)H (0.137 ml, 0.88 mmol). After stirring overnight at room temperature, the reaction was diluted with EtOAc, washed with H2O, brine and dried over MgSO4. The solvent was removed in vacuo and the crude product purified by column chromatography in hexane/EtOAc (1:1) to give the product (0.039 g, 11%). LC/MS: RT=2.830 min. 400/402 (MH+).

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customthe crude product purified by column chromatography in hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-c3bd33ea8e0c4fb5897e765f8b685acf
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

Loading…