Methyl iodide → HCID 57445085, compound

HRID 558132Notes

Reaction equation

HRID 558132 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[CH:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12].[CH3:21]I>CN(C=O)C.C(OCC)(=O)C>[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[CH:11]([N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57445086HCID 57445086, compound

Product 1

HCID 57445085HCID 57445085, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add sodium hydride (0.89 g, 22.4 mmol, 60% dispersion in mineral oil) to a solution of tert-butyl 1-(2-bromo-4-fluorophenyl)ethylcarbamate (4.75 g, 14.9 mmol) in DMF (10 mL). Stir the mixture for 30 min at RT. Add methyl iodide (1.86 mL, 29.9 mmol). Stir the mixture for 1 h at RT. Dilute with ethyl acetate, and wash with water and aqueous saturated sodium chloride. Dry over sodium sulfate and concentrate. Purify by column chromatography (hexane to 20% ethyl acetate in hexane) to give the title compound as a colorless oil (4.9 g, 98%). 1H NMR (400 MHz, CD3Cl) δ 1.32 (s, 9H), 1.45 (t, J=8.0 Hz, 3H), 2.58 (s, 3H), 5.39 (br, 1H), 7.00 (m, 1H), 7.28 (m, 2H).

Workup

  1. stirringStir the mixture for 1 h at RT
  2. washwash with water and aqueous saturated sodium chloride
  3. dry with materialDry over sodium sulfate
  4. concentrationconcentrate
  5. customPurify by column chromatography (hexane to 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4e0bd8ce99634f3db400de814ce27ac3
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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