5-Bromo-2-chloro-3-methylpyridine → benzyl (1S,5S)-6-(6-chloro-5-methyl-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

HRID 2251461Notes

Reaction equation

HRID 2251461 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.Br[C:19]1[CH:20]=[C:21]([CH3:26])[C:22]([Cl:25])=[N:23][CH:24]=1>>[Cl:25][C:22]1[N:23]=[CH:24][C:19]([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:20][C:21]=1[CH3:26]

Participants

3

Reactant 2

HCID 2854345-Bromo-2-chloro-3-methylpyridineHCID 23635906benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

Product 1

HCID 23635534benzyl (1S,5S)-6-(6-chloro-5-methyl-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylateYield 11%

Procedure

The product of Example 52D (1.30 g, 5.60 mmol) and 5-bromo-2-chloro-3-methylpyridine (1.73 g, 8.39 mmol) were processed according to the procedure described in Example 1E. The crude product was purified by chromatography (SiO2, ethyl acetate:hexane, 1:1) to provide the title compound (0.22 g, 11% yield) which was used directly in the next step without further purification. MS (DCI/NH3) m/z 358, 360 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-31d4f389efd04d2e862b10c388735975
Source dataset
uspto-grants-2008_01
Patent number
US07319106B2

Reaction notes

Loading…