Potassium Carbonate → n-(5-(4-((6-Cyanopyridin-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

HRID 885644Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:24]=[CH:23][C:12]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[N:19][CH:20]=3)=[CH:11][CH:10]=2)O1.Br[C:27]1[N:32]2[N:33]=[C:34]([NH:36][C:37]([CH:39]3[CH2:41][CH2:40]3)=[O:38])[N:35]=[C:31]2[CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[C:21]([C:18]1[N:19]=[CH:20][C:15]([CH2:14][O:13][C:12]2[CH:11]=[CH:10][C:9]([C:27]3[N:32]4[N:33]=[C:34]([NH:36][C:37]([CH:39]5[CH2:40][CH2:41]5)=[O:38])[N:35]=[C:31]4[CH:30]=[CH:29][CH:28]=3)=[CH:24][CH:23]=2)=[CH:16][CH:17]=1)#[N:22]

Participants

Conditions

Temperature: 90 °C

Procedure

5-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-pyridine-2-carbonitrile (10 g, 0.03 mol, 1.1 equiv.) was added to a solution of cyclopropanecarboxylic acid (5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide (7.6 g, 0.027 mol) in 1,4-dioxane/water (4:1; 70 mL). K2CO3 (7.45, 0.054 mol, 2 eq.) and PdCl2dppf (5%) were added to the solution. The resulting mixture was then heated in an oil bath at 90° C. under N2 until completion (monitored by LCMS). 1,4-Dioxane was removed under vacuum, and water/EtOAc were added and the solid was filtered. The obtained solid was dissolved in methanol/DCM, dried over MgSO4 and the final compound was obtained after purification by flash chromatography, eluted with neat EtOAc as a white solid

Workup

custom1,4-Dioxane was removed under vacuum, and water/EtOAc
additionwere added
filtrationthe solid was filtered
dissolutionThe obtained solid was dissolved in methanol/DCM
dry with materialdried over MgSO4

Sources & evidence

ORD record: ord-a1d06ea55bf14a09b527abac6bc88edc
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242274B2

Reaction notes

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