Tetrahydrofuran → HCID 86672865, compound

HRID 1036654Notes

Reaction equation

HRID 1036654 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[CH:10]=[C:4]2[CH:3]=1.[CH:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCCC1>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[C:14]1([CH3:17])[CH:15]=[CH:16][C:11]([C:9]2[CH:10]=[C:4]3[CH:3]=[C:2]([C:24]4[CH:25]=[C:20]([CH:21]=[CH:22][CH:23]=4)[CH:18]=[O:19])[CH:7]=[CH:6][N:5]3[N:8]=2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 27343563-Formylphenylboronic acidHCID 67254163HCID 67254163, compound

Product 1

HCID 86672865HCID 86672865, compoundYield 65.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The procedure described in stage 2.4 is followed, starting with 0.157 g (0.54 mmol) of 5-bromo-2-(p-tolyl)pyrazolo[1,5-a]pyridine obtained in stage 8.3, 0.098 g (0.65 mmol) of 3-formylphenylboronic acid, 0.535 g (1.64 mmol) of caesium carbonate and 0.045 g (0.055 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) in 5 ml of a 9/1 mixture of tetrahydrofuran and water. After chromatography on silica gel, elution being carried out with a mixture of cyclohexane and ethyl acetate (8/2), 0.110 g (65%) of the expected product is obtained in the form of a beige powder.

Workup

  1. washAfter chromatography on silica gel, elution
  2. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (8/2)

Sources & evidence

ORD record
ord-cc73b69f74384338a9893cc3bff296ec
Source dataset
uspto-grants-2013_10
Patent number
US08546424B2

Reaction notes

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