Triethylamine → 6-(Chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridine

HRID 709662Notes

Reaction equation

HRID 709662 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][C:4]1[N:9]=[C:8]([CH2:10]O)[CH:7]=[CH:6][C:5]=1[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[F:20].C(N(CC)CC)C.CS([Cl:34])(=O)=O>ClCCl>[Cl:34][CH2:10][C:8]1[N:9]=[C:4]([CH2:3][C:2]([CH3:22])([CH3:21])[CH3:1])[C:5]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[F:20])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 117759814(5-(2-Fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methanol

Product 1

HCID 1177599996-(Chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridineYield 64.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methanol (4.00 g) and triethylamine (4.00 g) in dichloromethane (20 mL) was added dropwise methanesulfonyl chloride (3.00 g) at 0° C., and the mixture was stirred at room temperature for 15 hr. Dichloromethane (150 ml) was added to the reaction mixture, and the mixture was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.75 g) as a colorless oil.

Workup

  1. washthe mixture was washed with saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9fb067e2e23b46008fcd6bb92f3db768
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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