Dimethylacetamide → 5-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

HRID 1472870Notes

Reaction equation

Br[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[C:4]([CH3:12])[CH:3]=1.[O:13]1[C:18]2[CH:19]=[CH:20][C:21](B(O)O)=[CH:22][C:17]=2[O:16][CH2:15][CH2:14]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC(N(C)C)=O>O>[O:13]1[C:18]2[CH:19]=[CH:20][C:21]([C:2]3[N:7]4[N:8]=[C:9]([NH2:11])[N:10]=[C:6]4[CH:5]=[C:4]([CH3:12])[CH:3]=3)=[CH:22][C:17]=2[O:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 150 °C

Procedure

5-Bromo-7-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (0.19 g, 0.84 mmol), 1,4-benzodioxane-6-boronic acid (0.18 g, 1.00 mmol), palladium(tetrakis)triphenylphosphine (97 mg, 0.084 mmol), potassium phosphate (0.36 g, 1.67 mmol), dimethylacetamide (3 ml) and water (1 ml) were added to a microwave vial containing a stirrer bar. The reaction was heated to 150° C. for 10 min. Water was added to the reaction mixture and the product extracted into ethyl acetate (×2). The organics were combined, washed several times with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with diethyl ether and collected by filtration to give the desired product. LCMS RT: 2.82 min, MI: 283.17, Method: 2

Workup

additioncontaining a stirrer bar
extractionthe product extracted into ethyl acetate (×2)
washwashed several times with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was triturated with diethyl ether
filtrationcollected by filtration

Sources & evidence

ORD record: ord-0a21cf6c0a834977846ae4400e3ce2bb
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012633B2

Reaction notes

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