Potassium Carbonate → 6-((8-bromo-7-(4-chlorophenyl)-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)nicotinonitrile

HRID 2101303

Reaction equation

[Br:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[NH:16][N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][N:28]=1>CN(C=O)C.O>[Br:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[N:16]([CH2:26][C:27]3[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][N:28]=3)[N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred mixture of 8-bromo-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (1.07 g, 3.31 mmol) in DMF (15 mL) at room temperature under argon was added K2CO3 (0.91 g, 6.62 mmol) and 6-(chloromethyl)nicotinonitrile (0.63 g, 4.14 mmol). The mixture was then heated to 60° C. for 7 h, after which HPLC indicated complete reaction. The mixture was cooled to room temperature, diluted with water (100 mL), and stirred for 30 min. Solid was collected by filtration and washed with water (10 mL×5), then methanol (3 mL×3), and finally dried under vacuum. The title compound (0.98 g) was obtained as a tan solid. HPLC/MS: retention time=3.4 min, [M+H]+=442.

Workup

customreaction
temperatureThe mixture was cooled to room temperature
filtrationSolid was collected by filtration
washwashed with water (10 mL×5)
dry with materialmethanol (3 mL×3), and finally dried under vacuum

Sources & evidence

ORD record: ord-cc9e7a8e9d5a4230987b1e622ba8425a
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572808B2

Linked notes

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