(4-Methoxyphenyl)boronic acid → HCID 67215454, compound

HRID 1677573Notes

Reaction equation

HRID 1677573 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O.Br[C:22]1[N:23]=[C:24]([C:31]([C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[C:35]([O:42][CH3:43])[CH:34]=2)=[O:32])[N:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=12>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:43][O:42][C:35]1[CH:34]=[C:33]([C:31]([C:24]2[N:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]3=[C:22]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:23]=2)=[O:32])[CH:38]=[CH:37][C:36]=1[N+:39]([O-:41])=[O:40]

Participants

6

Reactant 3

HCID 201262(4-Methoxyphenyl)boronic acidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 67215796HCID 67215796, compound

Product 1

HCID 67215454HCID 67215454, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

0.447 g (0.003 mol) of 4-methoxyphenylboronic acid, 2.24 g (0.009 mol) of K3PO4.H2O and then 0.131 g (0.011 mol) of tetrakis(triphenylphosphine)palladium(0) are added to 0.850 g (0.023 mol) of (1-bromoimidazo[1,5-a]pyridin-3-yl)(3-methoxy-4-nitrophenyl)methanone obtained in example 20 in 30 ml of dioxane under an argon atmosphere. The mixture is heated at reflux for 1 hour. The reaction medium is poured onto water and extracted with ethyl acetate. The organic phase is separated by settling, washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The product is purified by filtration through silica gel, elution being carried out with a dichloromethane/cyclohexane (2/1) mixture and then with dichloromethane. After evaporation, 0.850 g of an orange solid is collected. Melting point: 185° C.; 1H NMR (d6-DMSO): 3.85 (3H, s), 4.06 (3H, s), 7.12 (2H, d), 7.41-7.44 (1H, m), 7.54-7.58 (1H, m), 7.95 (2H, d), 8.08-8.10 (2H, m), 8.34 (1H, d), 8.36 (1H, s), 9.81 (1H, d)

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 1 hour
  3. additionThe reaction medium is poured onto water
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is separated
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. filtrationThe product is purified by filtration through silica gel, elution
  10. customAfter evaporation, 0.850 g of an orange solid
  11. customis collected

Sources & evidence

ORD record
ord-54117b2de5ae48fc8c5a383297b5651d
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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