Methyl iodide → N-((5-Bromopyridin-3-yl)methyl)-3-chloro-N-methylpicolinamide

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][C:10](=[O:18])[C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:5]=[N:6][CH:7]=1.[CH3:19]I.[H-].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]([CH3:19])[C:10](=[O:18])[C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:5]=[N:6][CH:7]=1

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 86679147N-((5-Bromopyridin-3-yl)methyl)-3-chloropicolinamide

Product 1

HCID 86679148N-((5-Bromopyridin-3-yl)methyl)-3-chloro-N-methylpicolinamide

Procedure

In analogy to the procedure described for the preparation of intermediate A-41, N-((5-bromopyridin-3-yl)methyl)-3-chloropicolinamide (intermediate A-56) was reacted with MeI in presence of NaH (60% in mineral oil) to give the title compound as a dark brown oil. MS: 340.2 and 342.2 (M+H+).

Sources & evidence

ORD record: ord-85cbf158a57d478791e753e0fa53063e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

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