5-Bromo-2-chloropyridine → Benzyl (cis)-6-(6-chloro-3-pyridinyl)-3,6-diazabicyclo[3,2,0]heptane-3-carboxylate

HRID 1817010Notes

Reaction equation

HRID 1817010 reaction equation
[C@@H:1]12[CH2:7][NH:6][C@@H:5]1[CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2]2.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][N:20]=1>>[Cl:18][C:19]1[N:20]=[CH:21][C:22]([N:6]2[CH2:7][C@@H:1]3[C@H:5]2[CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:2]3)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 27344145-Bromo-2-chloropyridineHCID 23635906benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

Product 1

HCID 23636264Benzyl (cis)-6-(6-chloro-3-pyridinyl)-3,6-diazabicyclo[3,2,0]heptane-3-carboxylateYield 38%

Procedure

The product of Example 52D (0.23 g, 1.0 mmol) and 2-chloro-5-bromopyridine (0.29 g, 1.5 mmol) were processed according to the procedure described in Example 1E. The crude product was purified by chromatography (SiO2, hexane:ethyl acetate, 60:40, Rf 0.3) to provide the title compound (0.13 g, 38% yield). 1H NMR (MeOH-d4, 300 MHz) δ 3.24 (dd, J=12.9, 4.1 Hz, 1H), 3.30 (m, 1H), 3.40 (m, 1H), 3.65 (dd, J=7.8, 3.4 Hz, 1H), 4.08-3.92 (m, 3H), 4.70 (dd, J=5.7, 3.7 Hz, 1H), 5.10 (m, 2H), 6.90 (dd, J=8.5, 3.1 Hz, 1H), 7.20 (d, J=8.8 Hz, 1H), 7.25 (m, 3H), 7.35 (m, 2H), 7.54 (d, J=3.0 Hz, 1H); MS (DCI/NH3) m/z 346 (M+2+H)+, 344 (M+H)+.

Workup

  1. customThe crude product was purified by chromatography (SiO2, hexane:ethyl acetate, 60:40, Rf 0.3)

Sources & evidence

ORD record
ord-d3f0503ae7e64080bafe10e5ed56251f
Source dataset
uspto-grants-2009_10
Patent number
US07598236B2

Reaction notes

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