Methyl iodide → tert-Butyl (4-bromopyridin-2-yl)(methyl)carbamate

HRID 2389648Notes

Reaction equation

HRID 2389648 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.[H-].[Na+].I[CH3:19]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]([CH3:19])[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11680626tert-butyl N-(4-bromopyridin-2-yl)carbamate

Product 1

HCID 59683608tert-Butyl (4-bromopyridin-2-yl)(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0° C. is added sodium hydride (53 mg, 1.32 mmol, 60% dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 μL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5% citric acid (10 mL) and extracted into EtOAc (2×10 mL). The combined organic phases are dried over Na2SO4 and purified by column chromatography (70% EtOAc in heptane) to give the title compound.

Workup

  1. stirringstirred 16 h
  2. customThe reaction is then quenched with 5% citric acid (10 mL)
  3. extractionextracted into EtOAc (2×10 mL)
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. custompurified by column chromatography (70% EtOAc in heptane)

Sources & evidence

ORD record
ord-f8b52b36d04c4fc986c6f7dfde6431b8
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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