Tetrahydrofuran → N-(4-chloro-3-(5-methylpyridin-2-yl)phenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamide

HRID 632976Notes

Reaction equation

HRID 632976 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[CH:30]=[CH:29][N:28]=[C:27]([Zn+])[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:27]1[CH:26]=[CH:25][C:30]([CH3:32])=[CH:29][N:28]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 66877122N-(4-Chloro-3-iodophenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamideHCID 178428692HCID 178428692, compound

Product 1

HCID 58614791N-(4-chloro-3-(5-methylpyridin-2-yl)phenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamide

Procedure

N-(4-Chloro-3-iodophenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamide (150 mg, 0.34 mmol) was used in Procedure B with 4-methyl-2-pyridylzinc bromide (1.7 mL of a 0.5 M in THF). Purified by silica gel chromatography (5-75% Ethyl acetate/Hexanes) to yield N-(4-chloro-3-(5-methylpyridin-2-yl)phenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamide as a white solid: TLC Rf=0.23 (35% ethyl acetate/hexanes); 1H NMR (CDCl3, 400 MHz) δ 10.62 (bs, 1H), 8.12 (dd, 1H), 7.89 (d, 1H), 7.58 (d, 1H), 7.47 (m, 3H), 7.18 (d, 1H), 6.89 (d, 1H), 2.62 (s, 3H), 2.38 (s, 3H); MS (Q1) 406.3 (M)+.

Workup

  1. customPurified by silica gel chromatography (5-75% Ethyl acetate/Hexanes)

Sources & evidence

ORD record
ord-b11ce6a5137544b5be547491694a45b8
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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