Benzoyl Peroxide → 5-Bromomethyl-2-(N,N-ditert-butoxycarbonylamino)PY

HRID 511552Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[N:6][CH:7]=1.C1C(=O)N([Br:30])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:30][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of di-tert-butyl (5-methylpyridin-2-yl)imidodicarbonate (Compound 309C, 5.66 g, 18.4 mmol), NBS (3.92 g, 22 mmol), and benzoyl peroxide (0.444 g, 1.84 mmol) in CCl4 (30 mL) was heated at 80° C. for 6 h. The mixture was cooled to room temperature, the solids were filtered off and the filtrate was concentrated. The residue was purified by silica gel chromatography (EtOAc/heptane: 1:1) to give 4.66 g of di-tert-butyl [5-(bromomethyl)pyridin-2-yl]imidodicarbonate (yield: 65%).

Workup

temperatureThe mixture was cooled to room temperature
filtrationthe solids were filtered off
concentrationthe filtrate was concentrated
customThe residue was purified by silica gel chromatography (EtOAc/heptane: 1:1)

Sources & evidence

ORD record: ord-cd216236cee74c229ac3a8afdfbd9bba
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096624B2

Reaction notes

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