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

HRID 922829Notes

Reaction equation

HRID 922829 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12](I)[CH:11]=2)=[O:8])=[C:5]([CH3:18])[O:4][N:3]=1.[Br-].C[C:21]1[C:22]([Zn+])=[N:23][CH:24]=[CH:25][CH:26]=1.[CH2:28]1COCC1>>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7]([C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH3:18])=[O:8])=[CH:11][C:12]=1[C:24]1[CH:25]=[CH:26][CH:21]=[C:22]([CH3:28])[N:23]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 668780383,5-dimethyl-N-(4-chloro-3-iodophenyl)isoxazole-4-carboxamideHCID 178426320HCID 178426320, compound

Product 1

HCID 58614728N-(4-chloro-3-(6-methylpyridin-2-yl)phenyl)-3,5-dimethylisoxazole-4-carboxamide

Procedure

Procedure B was performed with 3,5-dimethyl-N-(4-chloro-3-iodophenyl)isoxazole-4-carboxamide (190 mg, 0.5 mmol) and 3-methyl-2-pyridylzinc bromide (2.5 mL of a 0.5 M solution in THF). The crude reaction was purified by silica gel chromatography (5-100% Ethyl acetate/Hexanes) to yield N-(4-chloro-3-(6-methylpyridin-2-yl)phenyl)-3,5-dimethylisoxazole-4-carboxamide as a white solid: TLC Rf=0.43 (50% ethyl acetate/hexanes); 1H NMR (CDCl3, 400 MHz) δ 8.52 (bs, 1H), 7.68 (m, 2H), 7.48 (m, 3H), 2.70 (s, 3H), 2.49 (s, 3H), 2.21 (s, 3H); MS (Q1) 342.3 (M)+.

Workup

  1. customThe crude reaction
  2. customwas purified by silica gel chromatography (5-100% Ethyl acetate/Hexanes)

Sources & evidence

ORD record
ord-786476208e244a9aa07629951bdb1286
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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