Methyl iodide → 2-(N-BOC-N-methylamino)-5-bromopyridine

HRID 391098Notes

Reaction equation

HRID 391098 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].I[CH3:19]>C1COCC1>[C:4]([O:3][C:1](=[O:2])[N:8]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1)[CH3:19])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 162178432-(Boc-amino)-5-bromopyridine

Product 1

HCID 111969422-(N-BOC-N-methylamino)-5-bromopyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(BOC-amino)-5-bromopyridine (3.06 g) in THF (50 mL) was added sodium hydride (538 mg) and the reaction stirred at room temperature for 20 min. Then, iodomethane (0.84 mL) was added and the reaction stirred at room temperature for 16 h. The reaction was quenched with water (30 mL) and extracted into dichloromethane (3×30 mL). The organic layers were dried (MgSO4) and reduced in vacuo to give (5-bromo-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester as an oil.

Workup

  1. stirringthe reaction stirred at room temperature for 16 h
  2. customThe reaction was quenched with water (30 mL)
  3. extractionextracted into dichloromethane (3×30 mL)
  4. dry with materialThe organic layers were dried (MgSO4)

Sources & evidence

ORD record
ord-066a9c00441346abb9f849f80864cf79
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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