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

HRID 899445Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][NH:14][S:15]([CH2:18]CC)(=[O:17])=[O:16].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:29][C:30]1(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:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([N:14]([S:15]([CH3:18])(=[O:16])=[O:17])[CH2:13][CH2:29][CH3:30])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl 2,6-dichloroisonicotinate (10 g, 48.5 mmol), methyl(propylsulfonyl)amine (7.99 g, 58.2 mmol), potassium phosphate (14.4 g, 68 mmol), Xantphos (1.69 g, 2.9 mmol) and tris(dibenzylideneacetone)dipalladium (0.89 g, 0.97 mmol) were added to a dry, argon flushed flask. Dioxane (400 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, 0-35% EtOAc/hexanes) gave methyl 2-chloro-6-[(methylsulfonyl)(propyl)amino]isonicotinate as a yellow oil: 1H NMR (400 MHz, CD3OD) δ 7.88 (s, 1H), 7.72 (s, 1H), 3.96 (s, 3H), 3.91 (t, J=6.4 Hz, 2H), 3.13 (s, 3H), 1.68-1.53 (m, 2H), 0.93 (t, J=7.5 Hz, 3H).

Workup

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

Sources & evidence

ORD record: ord-fb26eca2608f4e239c65d0dffba5feee
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354942B2

Reaction notes

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