Methyl iodide → HCID 66607155, compound

HRID 563821Notes

Reaction equation

HRID 563821 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][N:24]([C:27](=[O:29])[CH3:28])[CH2:25][CH3:26])[CH:9]=[C:10]([Cl:12])[CH:11]=1)[CH3:2].[CH3:31][Si](C)(C)[N-][Si](C)(C)C.[Na+].IC.CCOC(C)=O>C1COCC1.O>[CH2:1]([O:3][C:4](=[O:30])[CH:5]([C:6]1[CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:20])[F:22])=[CH:15][C:14]=2[CH2:23][N:24]([C:27](=[O:29])[CH3:28])[CH2:25][CH3:26])[CH:9]=[C:10]([Cl:12])[CH:11]=1)[CH3:31])[CH3:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 66606899HCID 66606899, compound

Product 1

HCID 66607155HCID 66607155, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {2′-[(acetyl-ethyl-amino)-methyl]-5-chloro-4′-trifluoromethyl-biphenyl-3-yl}-acetic acid ethyl ester (0.070 g, 0.17 mmol) in THF at −78° C. under N2 was added sodium hexamethyldisilazide (1 M in THF; 0.20 mL, 0.20 mmol), and the mixture was stirred for 5 minutes. Iodomethane (0.01 mL, 0.20 mmol) was then added, and the reaction was stirred at −78° C. for 30 minutes. Once no starting material was seen by analytical LCMS, the mixture was worked-up with EtOAc and H2O, and the crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. stirringthe reaction was stirred at −78° C. for 30 minutes
  2. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8737383708834078a3539062f297706a
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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