Potassium Phosphate, Tribasic → Methyl 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinate

HRID 899466Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10](Cl)[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][NH:14][S:15]([CH3:18])(=[O:17])=[O:16].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:14]([CH3:13])[S:15]([CH3:18])(=[O:17])=[O:16])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl 2,6-dichloroisonicotinate (5.0 g, 24.3 mmol), methyl(methylsulfonyl)amine (3.18 g, 29.12 mmol), potassium phosphate (7.22 g, 34.0 mmol), Xantphos (0.87 g, 1.50 mmol) and tris(dibenzylideneacetone)dipalladium (0.68 g, 0.51 mmol) were added to a dry, argon flushed flask. Dioxane (195 mL) was added, the solution degassed with argon and the reaction was heated to 100° C. for 16 h. The reaction was cooled to rt, filtered through celite and evaporated in vacuo. Flash chromatography (silica, 0-50% EtOAc/CH2Cl2) gave methyl 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinate as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 7.88 (s, 1H), 7.68 (s, 1H), 3.96 (s, 3H), 3.44 (s, 3H), 3.11 (s, 3H).

Workup

customthe solution degassed with argon
temperatureThe reaction was cooled to rt
filtrationfiltered through celite
customevaporated in vacuo

Sources & evidence

ORD record: ord-f8547c07df7044bcaab567f293987591
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354942B2

Reaction notes

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