4-Chlorophenylboronic acid → HCID 67334858, compound

HRID 451460Notes

Reaction equation

HRID 451460 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[C:3]3[N:4]([N:8]=[C:9]([NH2:11])[N:10]=3)[CH:5]=[CH:6][CH:7]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 468640698-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine

Product 1

HCID 67334858HCID 67334858, compound

Reagents, catalysts & solvents 3

HCID 53485975CID 53485975CatalystHCID 10340Sodium CarbonateSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (500 mg, 2.35 mmol), 4-chlorophenyl boronic acid (757 mg, 4.69 mmol), dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium(II) dichloromethane adduct (153 mg, 0.188 mmol) and an aqueous solution of Na2CO3 (2 N, 2.35 mL, 4.69 mmol) in dioxane (10 mL) was stirred at 110° C. for 2 hours. The reaction mixture was diluted with a 2 N aqueous solution of sodium carbonate and extracted with diethyl ether, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using pentane/diethyl ether as eluent. The title compound was obtained as a white solid (572 mg, 99%).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. customthe solvent was evaporated
  4. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-0e13be44ac734e17b45cb79368380b74
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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