2-(Chloromethyl)-3-fluoropyridine → 6-Chloro-1-[(3-fluoropyridin-2-yl)methyl]-1H-indazole-3-carbonitrile

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]#[N:12])=[N:7][NH:8]2)=[CH:4][CH:3]=1.Cl[CH2:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][N:16]=1>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]#[N:12])=[N:7][N:8]2[CH2:14][C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 151336022-(Chloromethyl)-3-fluoropyridine

HCID 534084026-Chloro-1H-indazole-3-carbonitrile

Product 1

HCID 866921126-Chloro-1-[(3-fluoropyridin-2-yl)methyl]-1H-indazole-3-carbonitrileYield 92.7%

Procedure

2.3 g (12.95 mmol) of 6-chloro-1H-indazole-3-carbonitrile (WO 2011/149921, Expl. 58C) were reacted in analogy to Example 53A with 2.07 g (14.25 mmol) of 2-(chloromethyl)-3-fluoropyridine. 3.44 g of the title compound were obtained (93% of theory).

Sources & evidence

ORD record: ord-47da1088287f49998a06905243c81747
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023849B2

Reaction notes

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