Propargyl bromide → methyl 5-[N-tert-butoxycarbonyl-N-(prop-2-ynyl)amino]pyridine-2-carboxylate

HRID 1608527Notes

Reaction equation

HRID 1608527 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:19](Br)[C:20]#[CH:21]>>[C:1]([O:5][C:6]([N:8]([C:9]1[CH:10]=[CH:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[N:13][CH:14]=1)[CH2:21][C:20]#[CH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 7842Propargyl bromideHCID 14842342Methyl 5-(tert-Butoxycarbonylamino)picolinate

Product 1

HCID 14842343methyl 5-[N-tert-butoxycarbonyl-N-(prop-2-ynyl)amino]pyridine-2-carboxylateYield 90%

Procedure

Using the method described in J. Med. Chem., 1980, 23, 1405, methyl 5-(N-tert-butoxycarbonylamino)pyridine-2-carboxylate was reacted with prop-2-ynyl bromide to give methyl 5-[N-tert-butoxycarbonyl-N-(prop-2-ynyl)amino]pyridine-2-carboxylate in 90% yield. A mixture of the product so obtained and trifluoroacetic acid was stirred at 0° C. for 1 hour and evaporated. There was thus obtained methyl 5-(N-prop-2-ynylamino)pyridine-2-carboxylate in 90% yield, as a gum.

Sources & evidence

ORD record
ord-54f24d3d18c947e79885fcd15d6679f1
Source dataset
uspto-grants-1995_03
Patent number
US05395838

Reaction notes

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