Hydrogen Bromide → (6-Bromopyridin-2-yl)(1-methylpiperidin-4-yl)methanone

HRID 2366820Notes

Reaction equation

HRID 2366820 reaction equation
FC1C=C(F)C=C(F)C=1C(N[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[O:14])[N:8]=1)=O.C(N(CC)C(C1CCN(C)CC1)=O)C.[Br:42]C1C=CC=C(Br)N=1.Br>>[Br:42][C:7]1[N:8]=[C:9]([C:13]([CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[O:14])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 122742,6-DibromopyridineHCID 412858N,N-DIETHYL-1-METHYL-PIPERIDINE-4-CARBOXAMIDEHCID 11610526Lasmiditan

Product 1

HCID 17980300(6-Bromopyridin-2-yl)(1-methylpiperidin-4-yl)methanone

Procedure

The present invention is directed to a process for preparing 2,4,6-trifluoro-N-[6-(1-methyl-piperidine-4-carbonyl)-pyridin-2-yl]-benzamide or a pharmaceutically acceptable salt thereof e.g., the hemi-succinate salt comprising the step of: reacting N,N-diethyl-1-methylpiperidine-4-carboxamide (III) with a solution of 2,6-dibromopyridine and Grignard reagent followed by the addition of hydrobromic acid to yield (6-bromopyridin-2-yl)(1-methylpiperidin-4-yl)methanone (IV) hydrobromide.

Sources & evidence

ORD record
ord-4ad8d99074dd49c2aa7da8478c2f7864
Source dataset
uspto-grants-2014_04
Patent number
US08697876B2

Reaction notes

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