Potassium Carbonate → 5-[4-[(1,1-Dioxo-1,4-thiazinan-4-yl)methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 925498Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:23]=[CH:22][C:12]([CH2:13][N:14]3[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]3)=[CH:11][CH:10]=2)O1.Br[C:26]1[N:31]2[N:32]=[C:33]([NH2:35])[N:34]=[C:30]2[CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>O>[O:21]=[S:17]1(=[O:20])[CH2:16][CH2:15][N:14]([CH2:13][C:12]2[CH:11]=[CH:10][C:9]([C:26]3[N:31]4[N:32]=[C:33]([NH2:35])[N:34]=[C:30]4[CH:29]=[CH:28][CH:27]=3)=[CH:23][CH:22]=2)[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 90 °C

Procedure

4-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-thiomorpholine-1,1-dioxide (1.1 eq.) was added to a solution of 5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (4:1). K2CO3 (2 eq.) and PdCl2dppf (0.03 eq.) were added to the solution. The resulting mixture was then heated in an oil bath at 90° C. for 16 h under N2. Water was added and the solution was extracted with ethyl acetate. The organic layers were dried over anhydrous MgSO4 and evaporated in vacuo. The final compound was obtained after purification by flash chromatography.

Workup

extractionthe solution was extracted with ethyl acetate
dry with materialThe organic layers were dried over anhydrous MgSO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-fba7a9b36a9a4d10953e476b7a589483
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284311B2

Reaction notes

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