Tetrahydrofuran → N-(4-chloro-3-(3-methylpyridin-2-yl)phenyl)-6-(trifluoromethy)-2-methylpyridine-3-carboxamide

HRID 922825Notes

Reaction equation

HRID 922825 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-].C[C:25]1[N:30]=[C:29]([Zn+])[CH:28]=[CH:27][CH:26]=1.[CH2:32]1COCC1>>[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[C:26]([CH3:32])=[CH:27][CH:28]=[CH:29][N:30]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 66877122N-(4-Chloro-3-iodophenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamideHCID 178426002HCID 178426002, compound

Product 1

HCID 11661410N-(4-chloro-3-(3-methylpyridin-2-yl)phenyl)-6-(trifluoromethy)-2-methylpyridine-3-carboxamide

Procedure

N-(4-Chloro-3-iodophenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamide (142 mg, 0.32 mmol) was used in Procedure B with 6-methyl-2-pyridylzinc bromide (1.75 mL, of a 0.5 M in THF). Purified by silica gel chromatography (5-100% Ethyl acetate/Hexanes) to yield N-(4-chloro-3-(3-methylpyridin-2-yl)phenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamide as a white solid: TLC Rf=0.23 (30% ethyl acetate/hexanes); 1H NMR (CDCl3, 400 MHz) δ 8.81 (bs, 1H), 7.95 (dd, 1H), 7.67 (m, 3H), 7.53 (t, 2H), 7.38 (d, 1H), 7.07 (d, 1H), 2.71 (s, 3H), 2.43 (s, 3H); MS (Q1) 406.1 (M)+.

Workup

  1. customPurified by silica gel chromatography (5-100% Ethyl acetate/Hexanes)

Sources & evidence

ORD record
ord-b21b78c6d1fb491bb4421361909522a6
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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