3-Hydroxyazetidine hydrochloride → Methyl 2-(3-hydroxyazetidin-1-yl)-5-(trifluoromethyl)nicotinate

Reaction equation

Cl.[NH:2]1[CH2:5][CH:4]([OH:6])[CH2:3]1.Cl[C:8]1[N:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11]>>[OH:6][CH:4]1[CH2:5][N:2]([C:8]2[N:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])[CH2:3]1

Participants

Reactant 2

HCID 27592903-Hydroxyazetidine hydrochloride

HCID 72943191Methyl 2-chloro-5-(trifluoromethyl)nicotinate

Product 1

HCID 67958859Methyl 2-(3-hydroxyazetidin-1-yl)-5-(trifluoromethyl)nicotinateYield 82.6%

Procedure

The title compound (D67) (4.0 g) was prepared according to the experimental procedure described in Description 62 starting from azetidin-3-ol hydrochloride (2.3 g, 21.03 mmol) and methyl 2-chloro-5-(trifluoromethyl)nicotinate (D66) (4.2 g, 17.53 mmol)

Sources & evidence

ORD record: ord-a3e2fe36357b49219f228d8d1e090ab4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828987B2

Reaction notes

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