Methyl iodide → 4-Chloro-2-(2-methyl-thiophen-3-yl)-pyridine

HRID 910676Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][N:8]=1.[Li][CH2:15]CCC.CI.[NH4+].[Cl-]>CCOCC>[Cl:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([C:6]2[CH:5]=[CH:4][S:3][C:2]=2[CH3:15])[CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-(2-bromo-thiophen-3-yl)-4-chloro-pyridine (80 mg, 0.3 mmol) in Et2O (3 mL) at −78° C. was added n-BuLi (1.6 M in hexanes, 0.2 mL). After 10 min, MeI (70 mg, 0.5 mmol) was added. The resulting mixture was maintained at −78° C. for 2 h, then was warmed to room temperature and stirred for 3 h. The reaction mixture was treated with 2 M aqueous NH4Cl and extracted with EtOAc. The organic layer was dried and concentrated to yield a residue. The residue was purified by preparative TLC (hexanes/EtOAc) to yield 4-chloro-2-(2-methyl-thiophen-3-yl)-pyridine as a solid.

Workup

temperaturewas warmed to room temperature
extractionextracted with EtOAc
customThe organic layer was dried
concentrationconcentrated
customto yield a residue
customThe residue was purified by preparative TLC (hexanes/EtOAc)

Sources & evidence

ORD record: ord-f1fea8e45cfc46a2bcfa8018cc5086ec
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022209B2

Reaction notes

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