Trimethyltin chloride → 5-Chloro-2-(trimethylstannyl)pyridine

HRID 633028Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1)(=O)=O.[CH3:16][Sn:17](Cl)([CH3:19])[CH3:18]>>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([Sn:17]([CH3:19])([CH3:18])[CH3:16])=[N:8][CH:9]=1

Participants

Reactant 2

HCID 14016Trimethyltin chloride

HCID 117802885-Chloropyridin-2-yl trifluoromethanesulfonate

Product 1

HCID 219426435-Chloro-2-(trimethylstannyl)pyridine

Procedure

5-chloropyridin-2-yl trifluoromethanesulfonate (4.12 mmol) was used in Procedure I with trimethyltin chloride to yield 5-chloro-2-(trimethylstannyl)pyridine. The crude material (˜4 mmol) was used in Procedure K with N-(4-chloro-3-iodophenyl)-2-methyl-6-(trifluoromethyl)nicotinamide (2 mmol). Purified by silica gel chromatography (0-50% ethyl acetate/hexane) to yield N-(4-chloro-3-(5-chloropyridin-2-yl)phenyl)-2-methyl-6-(trifluoromethyl)nicotinamide as a white solid: TLC Rf=0.48 (25% ethyl acetate/hexanes); MS (Q1) 427 (M)+.

Sources & evidence

ORD record: ord-a2107a69e66643f9ba3917dc27485205
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321761B2

Reaction notes

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