Trimethylsilyldiazomethane → Methyl 6-fluoropyridine-3-carboxylate

HRID 1694832Notes

Reaction equation

HRID 1694832 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH3:11][Si](C=[N+]=[N-])(C)C>CO>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:11])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 2428196-Fluoronicotinic Acid

Product 1

HCID 13758765Methyl 6-fluoropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-fluoronicotinic acid (255 mg, 1.32 mmol) in methanol (5 mL) at room temperature was added (trimethylsilyl)diazomethane (4.0 mL, 2 M in diethyl ether, 8.0 mmol). The reaction mixture was stirred at room temperature for 30 min and concentrated. Methyl 6-fluoronicotinate (129 mg, 47%) was used without further purification: NMR (600 MHz, DMSO-d6) δ 8.79 (d, J=2.6 Hz, 1H), 8.47 (td, J=7.9, 2.6 Hz, 1H), 7.35 (ddd, J=8.5, 2.6, 0.6 Hz, 1H), 3.88 (s, 3H); ESIMS calcd 156.0 (M++H), found 156.1 (M++H).

Workup

  1. concentrationconcentrated
  2. customMethyl 6-fluoronicotinate (129 mg, 47%) was used without further purification

Sources & evidence

ORD record
ord-15b797423f4241f0b8b1a315f9e2a239
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

Loading…