2-Bromopyridine → HCID 22065978, compound

HRID 1828279Notes

Reaction equation

[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1>>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:4]1[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3]1

Participants

Reactant 2

HCID 79732-Bromopyridine

HCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 22065978HCID 22065978, compound

Conditions

Temperature: 150 °C

Procedure

tert-Butyl 1,4-diazepane-1-carboxylate (5.0 g, 25.0 mmol) (Aldrich) and 2-bromopyridine (1.98 g, 12.50 mmol) (Aldrich) were combined in a sealed tube and heated at 150° C. for 12 hours. The mixture was purified by flash chromatography (5% MeOH/CH2Cl2) to provide the title compound. 1H NMR (CDCl3, 300 MHz) δ 1.48 (m, 9H), 1.88–2.02 (m, 2H), 3.20–3.48 (m, 2H), 3.52–3.70 (m, 4H), 3.72–3.83 (m, 2H), 6.45–6.59 (m, 2H), 7.47 (m, 2H), 8.11–8.18 (m, 1H); MS (DCI/NH3) m/z 278 (M+H)+.

Workup

customThe mixture was purified by flash chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-b5bcd3701c6a400b93e1b95ebf070184
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07057042B2

Reaction notes

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