Dimethyl Sulfoxide → 4-(2-chloropyridin-3-yl)-N-methylpyridin-2-amine

HRID 446297Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10](F)[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH3:16][NH2:17].C([O-])([O-])=O.[K+].[K+].CS(C)=O>O>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:17][CH3:16])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To 2-chloro-2′-fluoro-[3,4′]bipyridinyl (5.30 g, 25.4 mmol), methylamine hydrochloride (9.00 g, 133 mmol) and K2CO3 (28.1 g, 203 mmol) was added DMSO (70 mL). The mixture was heated overnight at 80° C. in a sealed tube. The cooled mixture was diluted with water (300 mL) and the resulting solid was filtered, washed with water and dried to yield (2-chloro-[3,4′]bipyridinyl-2′-yl)-methyl-amine. MS m/z=220 [M+1]+. Calc'd for C11H10ClN3: 219.68.

Workup

filtrationthe resulting solid was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-e201cdedcea9464aae1710a45b6f3f7c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476434B2

Reaction notes

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