N-(4-Chloro-3-iodophenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamide → N-(4-chloro-3-(pyridin-2-yl)phenyl)-2-methyl-6-(trifluoromethyl)nicotinamide

HRID 632982Notes

Reaction equation

HRID 632982 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12]([CH3:21])=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)=[O:10])=[CH:4][C:3]=1I.[Br-].[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Zn+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12]([CH3:21])=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)=[O:10])=[CH:4][C:3]=1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=1

Participants

3

Reactant 2

HCID 66877122N-(4-Chloro-3-iodophenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamideHCID 178418723HCID 178418723, compound

Product 1

HCID 44626323N-(4-chloro-3-(pyridin-2-yl)phenyl)-2-methyl-6-(trifluoromethyl)nicotinamide

Procedure

Procedure B was performed using N-(4-Chloro-3-iodophenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamide (88 mg, 0.2 mmol) with 2-pyridylzinc bromide (1 mL, 0.5 mmol, 0.5 M in THF). Purified by silica gel chromatography (10-80% ethyl acetate/hexanes) to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamide as a yellow solid: TLC Rf=0.28 (35% ethyl acetate/hexanes); TLC Rf=0.28 (35% ethyl acetate/hexanes); NMR (CDCl3, 400 MHz) 8.88 (bs, 1H), 8.41 (d, 1H), 7.96 (dd, 1H), 7.74 (m, 4H), 7.52 (d, 1H), 7.22 (m, 1H), 2.75 (s, 3H); MS (Q1) 392 (M)+.

Workup

  1. customPurified by silica gel chromatography (10-80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a0678b6b1a4041f4b195bacdf3a9d4bb
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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