Triethylamine → 3-(Chloromethyl)-2-methoxypyridine

HRID 1716291Notes

Reaction equation

HRID 1716291 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9]O)=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.CS([Cl:22])(=O)=O>C(Cl)Cl>[Cl:22][CH2:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10630565(2-Methoxypyridin-3-yl)methanol

Product 1

HCID 149329453-(Chloromethyl)-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-methoxy-pyridin-3-yl)-methanol (0.38 g, 2.74 mmol) from example 42 step A and triethylamine (0.5 mL, 3.56 mmol) in 6 mL of CH2Cl2 was added methanesulfonyl chloride (0.26 mL, 3.29 mmol) at 0° C. After 1 hr, the reaction was warmed to room temperature and stirred overnight. The reaction mixture was brought to the usual work-up to give the crude product, which was purified by chromatography (silica gel, 25% EtOAc/hexanes). 1H NMR (300 MHz, CDCl3) 8.15 (m, 1H), 7.67 (m, 1H), 6.91 (m, 1H), 4.60 (s, 2H), 4.02 (s, 3H).

Sources & evidence

ORD record
ord-4f4f5d453c98442380bd40f0e48ef305
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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