Tetrahydrofuran → HCID 86672864, compound

HRID 1036651Notes

Reaction equation

HRID 1036651 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[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>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]1[CH:10]=[C:4]2[CH:3]=[C:2]([C:24]3[CH:25]=[C:20]([CH:21]=[CH:22][CH:23]=3)[CH:18]=[O:19])[CH:7]=[CH:6][N:5]2[N:8]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 27343563-Formylphenylboronic acidHCID 70375558HCID 70375558, compound

Product 1

HCID 86672864HCID 86672864, compoundYield 79%

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 0.150 g (0.52 mmol) of 5-bromo-2-(2-fluorophenyl)pyrazolo[1,5-a]pyridine obtained in stage 7.1, 0.092 g (0.61 mmol) of 3-formylphenylboronic acid, 0.502 g (1.54 mmol) of caesium carbonate and 0.042 g (0.050 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), 0.130 g (79%) 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-18120a3754a4430ea6d383f9fa41dc29
Source dataset
uspto-grants-2013_10
Patent number
US08546424B2

Reaction notes

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