Pyrrolidine → 2-(Pyrrolidin-1-yl)-6-(trifluoromethyl)pyridine-3-carboxylic acid

Reaction equation

Cl[C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>>[N:15]1([C:2]2[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 27782102-Chloro-6-(trifluoromethyl)nicotinic acid

Product 1

HCID 670469932-(Pyrrolidin-1-yl)-6-(trifluoromethyl)pyridine-3-carboxylic acidYield 95.2%

Procedure

A mixture of 2-chloro-6-(trifluoromethyl)nicotinic acid (purchased from APOLLO, 5.0 g, 22.2 mmol) and pyrrolidine (40 ml, 562 mmol) was stirred for 24 hours at room temperature according to J. Med. Chem., 2005, 48, 71-90). Then the reaction mixture was evaporated in vacuo to give the title compound (5.5 g, 95%).

Workup

customThen the reaction mixture was evaporated in vacuo

Sources & evidence

ORD record: ord-08f513b71c6349f99ec8f19e24965fb3
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622589B2

Reaction notes

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