Iodoethane → HCID 22143614, compound

HRID 1825152Notes

Reaction equation

HRID 1825152 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[NH:7][C:6]=1[CH3:16])=[O:4].[CH2:19](I)[CH3:20].[H-].[Na+]>C1COCC1>[CH2:19]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[C:5]([C:3](=[O:4])[C:2]([F:1])([F:17])[F:18])=[C:6]1[CH3:16])[CH3:20]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 22143617HCID 22143617, compound

Product 1

HCID 22143614HCID 22143614, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,2,2-trifluoro-1-(6-methoxy-2-methyl-1H-indol-3-yl)-ethanone 71a (1.3 g, 5.05 mmole) in 20 ml anhydrous THF was added ethyl iodide (2.36 g, 15.15 mmole) and sodium hydride (404 mg, 60% in mineral oil, 10.1 mmole) with ice bath cooling. The mixture was warmed slowly to room temperature and stirred for an additional four hours. The reaction was quenched with water and extracted with EtOAc. The combined organic layer was dried over Na2SO4, filtered and concentrated under rot vap. The residue was purified by column chromatography (eluting with 20–30% EtOAc in hexanes) to give a brown oil (580 mg, 40% yield). 1H NMR (300 MHz, CDCl3) δ 7.91 (1H, d, J=8.9 Hz), 6.93 (1H, dd, J=2.3, 8.9 Hz), 6.82 (1H, d, J=2.3 Hz), 4.18 (2H, m), 3.88 (3H, s), 2.76 (3H, s), 1.40 (3H, m).

Workup

  1. temperaturecooling
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under rot vap
  7. customThe residue was purified by column chromatography (eluting with 20–30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e886b3fba9f14f26890ca0f36e371efd
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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