Tetrahydrofuran → 2,6-Difluoro-3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehyde

HRID 1036649Notes

Reaction equation

HRID 1036649 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]([F:17])=[CH:13][CH:12]=3)[CH:10]=[C:4]2[CH:3]=1.[F:18][C:19]1[C:24]([CH:25]=[O:26])=[C:23]([F:27])[CH:22]=[CH:21][C:20]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCCC1>C(OCC)(=O)C.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[F:18][C:19]1[C:20]([C:2]2[CH:7]=[CH:6][N:5]3[N:8]=[C:9]([C:11]4[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=4)[CH:10]=[C:4]3[CH:3]=2)=[CH:21][CH:22]=[C:23]([F:27])[C:24]=1[CH:25]=[O:26]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 32889552,4-Difluoro-3-formylphenylboronic acidHCID 67255182HCID 67255182, compound

Product 1

HCID 866728612,6-Difluoro-3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehydeYield 76.6%

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 0.300 g (1.03 mmol) of 5-bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine obtained in stage 2.3, 0.210 g (1.13 mmol) of 2,4-difluoro-3-formylphenylboronic acid, 1.00 g (3.09 mmol) of caesium carbonate and 0.084 g (0.10 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), 0.278 g (76%) of the expected product is obtained in the fowl 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-6d5d540f3453409085c9055f8d005b8c
Source dataset
uspto-grants-2013_10
Patent number
US08546424B2

Reaction notes

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