Methyl iodide → HCID 86584524, compound

HRID 1636403Notes

Reaction equation

HRID 1636403 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[O:6][C:7]1[N:12]=[C:11]([O:13][C:14]2[CH:15]=[C:16]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:17]=[CH:18][CH:19]=2)[C:10]([F:25])=[C:9]([CH3:26])[C:8]=1[F:27])#[N:2].CI.N1(C2CCCCCCCCCC2)CCCCCCCC[CH2:35]N1>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[O:6][C:7]1[N:12]=[C:11]([O:13][C:14]2[CH:15]=[C:16]([CH2:20][CH2:21][C:22]([O:24][CH3:35])=[O:23])[CH:17]=[CH:18][CH:19]=2)[C:10]([F:25])=[C:9]([CH3:26])[C:8]=1[F:27])#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23441739HCID 23441739, compoundHCID 57346892Diazabicycloundecane

Product 1

HCID 86584524HCID 86584524, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-[(6-(3-cyanophenoxy)-3,5-difluoro-4-methylpyridin-2-yl)oxy]benzenepropionic acid (0.50 g, 1.2 mmol) in methylene chloride (20 mL) was added methyl iodide (0.26 g, 1.8 mmol) and diazabicycloundecane (2.8 g, 1.8 mmol). After stirring for 15 hours, the solution was concentrated in vacuo and chromatographed on silica gel with ethyl acetate/hexane (1/4) to give 3-[(6-(3-cyanophenoxy)-3,5-difluoro-4-methylpyridin-2-yl)oxy]benzenepropionic acid, methyl ester; NMR (CDCl3) 7.3 (m,5), 7.05 (d, l), 6.85 (m,2), 3.68 (s,3), 2.9 (t,2), 2.55 (t,2), 2.4 (s,3) ppm.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customchromatographed on silica gel with ethyl acetate/hexane (1/4)

Sources & evidence

ORD record
ord-a7b94c2b9ba34d9f882f159e7b1e0c9d
Source dataset
uspto-grants-2000_03
Patent number
US06034103

Reaction notes

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