Dichloromethane → HCID 67337313, compound

HRID 451452Notes

Reaction equation

HRID 451452 reaction equation
[NH2:1][C:2]1[N:15]=[C:5]2[C:6](Br)=[CH:7][CH:8]=[C:9]([C:10]([OH:13])([CH3:12])[CH3:11])[N:4]2[N:3]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>O1CCOCC1.O>[NH2:1][C:2]1[N:15]=[C:5]2[C:6]([C:20]3[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=3)=[CH:7][CH:8]=[C:9]([C:10]([OH:13])([CH3:12])[CH3:11])[N:4]2[N:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 67335149HCID 67335149, compound

Product 1

HCID 67337313HCID 67337313, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(2-amino-8-bromo-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-propan-2-ol (contaminated with ketone) (120 mg, 0.443 mmol) and 4-chlorophenyl boronic acid (155 mg, 0.987 mmol) in dioxane (6 mL) was added aqueous solution of Na2CO3 (2 M, 0.72 mL) and degassed with argon for 5 minute. To this was added PdCl2 (dppf)2.CH2Cl2 (30.34 mg, 0.04 mmol) and stirred at 90° C. for 90 minutes. The reaction mixture was cooled to room temperature and water (20 mL) was added. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue was purified by silica gel chromatography using ethyl acetate/hexane as eluent. The title compound was obtained as an off white solid (65 mg, 48%) which was contaminated with 1-[2-amino-8-(4-chloro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-ethanone.

Workup

  1. customdegassed with argon for 5 minute
  2. additionTo this was added PdCl2 (dppf)2
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. customthe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7fcf56dc98744dd58cceac0342f40f38
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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