Methylamine → 4-(6-(fluoromethyl)pyridin-2-yl)-N-methylbut-3-yn-1-amine

HRID 334763Notes

Reaction equation

HRID 334763 reaction equation
CS(O[CH2:6][CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][F:17])[N:11]=1)(=O)=O.[CH3:18][NH2:19]>>[F:17][CH2:16][C:12]1[N:11]=[C:10]([C:9]#[C:8][CH2:7][CH2:6][NH:19][CH3:18])[CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 866302534-(6-(Fluoromethyl)pyridin-2-yl)but-3-ynyl methanesulfonate

Product 1

HCID 665983664-(6-(fluoromethyl)pyridin-2-yl)-N-methylbut-3-yn-1-amineYield 15%

Procedure

The title compound was prepared in accordance with the general method of Example 199(C), from 4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl methanesulfonate (2.90 g, 11 mmol) and N-methylamine 40% in aqueous solution (20 mL). The crude residue was purified over silicagel chromatography (prepacked 70 g silicagel column, DCM/MeOH: from 90/10 to 90/10 with 1% TEA as eluent) to afford 324 mg of 4-(6-(fluoromethyl)pyridin-2-yl)-N-methylbut-3-yn-1-amine as a pale oil (Yield: 15%).

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 70 g silicagel column, DCM/MeOH: from 90/10 to 90/10 with 1% TEA as eluent)

Sources & evidence

ORD record
ord-46c5c753d3cf4e72814f935158f41717
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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