Azobisisobutyronitrile → Di-tert-butyl [6-(bromomethyl)pyridin-3-yl]imidodicarbonate

HRID 1948080Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of di-tert-butyl (6-methylpyridin-3-yl)imidodicarbonate (Compound 260D, 15 g, 49 mmol), NBS (8.2 g, 49 mmol) and AIBN (1.0 g) in CCl4 (200 mL) was stirred at 100° C. overnight. TLC showed the reaction was complete. The reaction mixture was concentrated and residue was purified by column chromatography to afford the desired compound (5.0 g, yield: 26%) as a yellow solid. 1H NMR (CDCl3, 400 MHz): δ=1.41 (s, 18H), 4.53 (s, 2H), 7.44 (dd, J=2.4, 8.0 Hz, 1H), 7.67 (d, J=8.4 Hz, 1H), 8.33 (dd, J=2.4, 8.0 Hz, 1H).

Workup

concentrationThe reaction mixture was concentrated
customresidue was purified by column chromatography

Sources & evidence

ORD record: ord-88bf2324aa364c7e9e404fc7d042570f
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399433B2

Reaction notes

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