Methyl iodide → 3-Chloro-5-[(3-chloro-2-methoxy-6-methylpyridin-4-yl)oxy]benzonitrile

HRID 1952341Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[C:15]([CH3:17])[NH:14][C:13](=[O:18])[C:12]=2[Cl:19])[CH:9]=1)[C:5]#[N:6].[CH3:20]I>C(=O)([O-])[O-].[Ag+2].C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]([O:18][CH3:20])[C:12]=2[Cl:19])[CH:9]=1)[C:5]#[N:6]

Participants

Conditions

Temperature: 50 °C

Procedure

Compound 3-4 (2.45 g; 8.32 mmol), methyl iodide (1.573 mL; 25.2 mmol), silver carbonate (3.28 g; 11.89 mmol) and chloroform (100 mL) were added to a sealed vessel. The contents of the sealed vessel were heated at 50° C. for 3 hours in the absence of light. The reaction was cooled to room temperature, the insoluble material filtered off, and the filtrate concentrated in vacuo. The crude material was purified via silica gel chromatography (0-10% EtOAc in hexane) to give the title compound. MS M+1=308.9. 1H NMR (CDCl3): 2.42 (s, 3H), 4.05 (s, 3H), 6.36 (s, 1), 7.16 (m, 1H), 7.24 (m, 1H), 7.44 (m, 1H).

Workup

temperatureThe reaction was cooled to room temperature
filtrationthe insoluble material filtered off
concentrationthe filtrate concentrated in vacuo
customThe crude material was purified via silica gel chromatography (0-10% EtOAc in hexane)

Sources & evidence

ORD record: ord-e8ec47d1f58a4627a8af757153316dfa
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404856B2

Reaction notes

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