Methyl iodide → HCID 66934270, compound

HRID 881493Notes

Reaction equation

HRID 881493 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([Br:15])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:20]>C1COCC1>[C:1]([O:5][C:6](=[O:16])[N:7]([C:8]1[C:13]([CH3:14])=[CH:12][C:11]([Br:15])=[CH:10][N:9]=1)[CH3:20])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57345806tert-Butyl (5-bromo-3-methylpyridin-2-yl)carbamate

Product 1

HCID 66934270HCID 66934270, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-bromo-3-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester (409 mg) in THF (20 mL) was added sodium hydride (68 mg) and the reaction was stirred at room temperature for 20 min. Then, iodomethane (0.11 mL) was added and the reaction was stirred at room temperature for 16 h. The reaction was quenched with water (30 mL) and extracted into ethylacetate (2×20 mL). The organic layers were washed with brine (2×40 mL), dried (MgSO4) and reduced in vacuo to give (5-bromo-3-methyl-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester as a yellow oil.

Workup

  1. stirringthe reaction was stirred at room temperature for 16 h
  2. customThe reaction was quenched with water (30 mL)
  3. extractionextracted into ethylacetate (2×20 mL)
  4. washThe organic layers were washed with brine (2×40 mL)
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-25e0bf9dd59e4e64966baba9f14d0797
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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