1,2-Dichloroethane → 1-(5-Iodo-1H-indol-1-yl)ethanone

HRID 1057126Notes

Reaction equation

HRID 1057126 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(N(CC)CC)C.[C:18](OC(=O)C)(=[O:20])[CH3:19].ClCCCl>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:18](=[O:20])[CH3:19])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 27823135-Iodo-1H-indole

Product 1

HCID 668025481-(5-Iodo-1H-indol-1-yl)ethanoneYield 96.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-iodo-1H-indole (530 mg, 2.18 mmol), DMAP (53 mg, 0.43 mmol), triethylamine (0.46 mL, 3.30 mmol), acetic anhydride (0.81 mL, 8.57 mmol), and 1,2-dichloroethane (5.5 mL) was heated at 60° C. overnight. The reaction mixture was diluted with ethyl acetate (100 mL), washed (50 mL saturated NH4Cl then 50 mL brine), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield the title compound as a white solid (600 mg, 96%). 1H NMR (300 MHz, DMSO-d6): δ 8.17 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.58 (dd, 1H), 6.70 (d, 1H), 2.64 (s, 3H).

Workup

  1. washwashed (50 mL saturated NH4Cl
  2. dry with material50 mL brine), dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d18ed04a6367489585f59989be671c46
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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