Chlorosuccinimide → 6-bromo-3,5-dichloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyridin-2-amine

HRID 1963889Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:5]([Cl:16])=[CH:4][C:3]=1[Cl:17].BrC1N=C(NCC2CCOCC2)C(Cl)=CC=1.C1C(=O)N(Cl)C(=O)C1>C(#N)C>[Br:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[C:5]([Cl:16])=[CH:4][C:3]=1[Cl:17]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of a mixture of 6-bromo-3,5-dichloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyridin-2-amine/6-bromo-3-chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyridin-2-amine (4.5 g, ratio ˜2:3) in acetonitrile (40 mL) was added NCS (1.250 g, 9.36 mmol). The mixture was heated to 80° C. for 50 min. The mixture was allowed to cool to ambient temperature and concentrated in vacuo. The resulting residue was purified by column chromatography [SiO2, 120 g, EtOAc/heptane] providing 6-bromo-3,5-dichloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyridin-2-amine as white solid. Yield: 2.25 g. LCMS (m/z): 340.9[M+H]+; Retention time=1.11 min.

Workup

temperatureto cool to ambient temperature
concentrationconcentrated in vacuo
customThe resulting residue was purified by column chromatography [SiO2, 120 g, EtOAc/heptane]

Sources & evidence

ORD record: ord-d9eb8aa397e444428d9befe82a1ca2b8
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415381B2

Reaction notes

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