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

HRID 1054416
Notes
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Reaction equation

HRID 1054416 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 62657Potassium Phosphate, TribasicHCID 2776178(2,3-Dihydro-1,4-benzodioxin-6-yl)boronic acidHCID 595896855-Bromo-7-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 595895355-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

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

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

Sources & evidence

ORD record
ord-658c5b24fced41328aec850f62536c82
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394301B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes