Methyl iodide → 1454913-72-4

HRID 1398450Notes

Reaction equation

HRID 1398450 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[F:11].[CH2:12]1CCN2C(=NCCC2)CC1.IC>C(#N)C>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:12])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[F:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 114579884-chloro-5-fluoropyridine-3-carboxylic acid

Product 1

HCID 866959231454913-72-4Yield 65.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-chloro-5-fluoronicotinic acid (1.7 g, 9.68 mmol) in acetonitrile (18 mL) cooled to 0° C. was added DBU (3.65 mL, 24.21 mmol) dropwise. The reaction mixture was stirred for 30 min. To this mixture iodomethane (3.03 mL, 48.4 mmol) was added dropwise and stirred at rt for 12 h. The volatiles were removed under reduced pressure. The residue was purified via silica gel column chromatography (hexane and ethyl acetate) to afford methyl 4-chloro-5-fluoronicotinate (1.2 g, 6.33 mmol, 65% yield) as a yellow solid. LC/MS (ESI) m/e 190.0 [(M+H)+, calcd for C7H6ClFNO2 189.9]; LC/MS retention time (method D): tR=0.77 min.

Workup

  1. stirringstirred at rt for 12 h
  2. customThe volatiles were removed under reduced pressure
  3. customThe residue was purified via silica gel column chromatography (hexane and ethyl acetate)

Sources & evidence

ORD record
ord-4e9a630db9a94cae8443f414ddd2c21f
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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