Methyl iodide → (5-Bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester

HRID 627314Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[C:10]([N+:15]([O-:17])=[O:16])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:19]1CCN2C(=NCCC2)CC1.CI>CN(C=O)C>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([N:7]([CH3:19])[C:6](=[O:18])[OH:5])=[N:9][C:10]=1[N+:15]([O-:17])=[O:16].[C:1]([O:5][C:6](=[O:18])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[C:10]([N+:15]([O-:17])=[O:16])[N:9]=1)[CH3:19])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (5-bromo-6-nitro-pyridin-2-yl)-carbamic acid tert-butyl ester (11) (4.2 g, 13.2 mmol) in dry DMF (21 mL), DBU (5.02 g, 33.0 mmol)! was added at 0° C. Methyl iodide (3.75 g, 26.4 mmol) was added slowly at 0° C. After stirring for 3 hours at 0° C. the reaction mixture was quenched and the product was precipitated upon addition of aqueous NaHSO4(1M). The crude product was isolated by filtration and purified by recrystallisation from a mixture of MeCN and water to afford (5-bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid ten-butyl ester 12 (1.55 g).

Workup

additionwas added at 0° C
customwas quenched
customthe product was precipitated upon addition of aqueous NaHSO4(1M)
customThe crude product was isolated by filtration
custompurified by recrystallisation from a mixture of MeCN and water

Sources & evidence

ORD record: ord-85555ed0cc8e448badfa4f77c707e3e8
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309267B2

Reaction notes

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