2-Bromopyridine → HCID 67376913, compound

HRID 2377679Notes

Reaction equation

[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1>O1CCOCC1>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

Conditions

Temperature: 150 °C

Procedure

tert-Butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1.0 g, 5.10 mmol, Aldrich) in 1,4-dioxane (10 mL) in a sealed tube was treated with 2-bromopyridine (0.40 g, 2.50 mmol, Aldrich) and heated at 150° C. for 12 hours. The mixture was allowed to cool to room temperature and was concentrated under reduced pressure. The residue was purified by flash chromatography (5% MeOH/CH2Cl2) to provide the title compound. 1H NMR (CDCl3, 300 MHz) δ 1.48 (m, 9H), 1.86-1.94 (m, 2H), 3.30-3.58 (m, 4H), 4.52 (brs, 0.5H), 4.67 (brs, 0.5H), 4.80 (brs, 0.5H), 4.92 (brs, 0.5H), 6.32 (d, J=9.0 Hz, 1H), 6.57 (t, J=6.0 Hz, 1H), 7.38-7.55 (m, 1H), 8.12 (d, J=6.0 Hz, 1H). MS (DCI/NH3) m/z 276 (M+H)+.

Workup

temperatureto cool to room temperature
concentrationwas concentrated under reduced pressure
customThe residue was purified by flash chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-d8de984670824f97b3902df5754a534a
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470691B2

Reaction notes

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