Trimethylsilyldiazomethane → Methyl 2-chloro-5-fluoronicotinate

HRID 72434Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][Si](C=[N+]=[N-])(C)C>>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

Reactant 2

HCID 167693Trimethylsilyldiazomethane

HCID 114352432-Chloro-5-fluoronicotinic acid

Product 1

HCID 24229209Methyl 2-chloro-5-fluoronicotinateYield 83.4%

Procedure

The title compound (D69) (0022/105/1) (1.8 g) was prepared according to the experimental procedure described in Description 66 starting from 2-Chloro-5-fluoronicotinic acid (2 g, 11.39 mmol) and trimethylsilyldiazomethane (2M solution in diethyl ether) (17 ml, 34.18 mmol)

Sources & evidence

ORD record: ord-3f6d446cdb1b4a22937cf879919aa8b4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828987B2

Reaction notes

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