5-fluoropyridine-2-carboxylic Acid → Methyl 5-fluoropyridine-2-carboxylate

HRID 1643633Notes

Reaction equation

HRID 1643633 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10](F)=[CH:9][C:8]([F:12])=[CH:7][N:6]=1)=[O:4].FC1C=CC(C(O)=O)=NC=1>>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:12])=[CH:7][N:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 27628765-fluoropyridine-2-carboxylic AcidHCID 46311137Methyl 3,5-difluoropyridine-2-carboxylate

Product 1

HCID 23053520Methyl 5-fluoropyridine-2-carboxylate

Procedure

The title compound was prepared in a similar manner as described for Intermediate 175a, from 5-fluoropicolinic acid (1.05 g, 7.44 mmol) to give a yellow solid (980 mg, 85% yield). 1H NMR (400 MHz, CDCl3) δ 8.59 (d, J=2.78 Hz, 1 H) 8.21 (dd, J=8.72, 4.42 Hz, 1 H) 7.55 (d, J=3.03 Hz, 1 H) 4.02 (s, 3 H); LCMS for C7H6FNO2 m/z 156.00 (M+H+).

Sources & evidence

ORD record
ord-3576d40beaef42dca476c1e3a11994b7
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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