Cesium carbonate → HCID 53241137, compound

HRID 1918200Notes

Reaction equation

HRID 1918200 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]([Cl:17])=[CH:13][CH:12]=3)[CH:10]=[C:4]2[CH:3]=1.[CH3:18][O:19][C:20]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[CH:10]=[C:4]3[CH:3]=[C:2]([C:26]4[CH:27]=[C:22]([CH:23]=[CH:24][CH:25]=4)[C:20]([O:19][CH3:18])=[O:21])[CH:7]=[CH:6][N:5]3[N:8]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 67254097HCID 67254097, compound

Product 1

HCID 53241137HCID 53241137, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

The procedure described in Example 3 is followed. Starting from 1.5 g (4.88 mmol) of 5-bromo-2-(4-chlorophenyl)pyrazolo[1,5-a]pyridine, obtained according to the protocol described in Examples 1.3 or 2.3, 1.05 mg (5.83 mmol) of 3-methoxycarbonylphenylboronic acid, 4.6 g (14.61 mmol) of caesium carbonate, 0.400 g (0.49 mmol) of [1,1′-bis(diphenyl-phosphino)ferrocene]dichloropalladium(II) and 20 ml of a THF/water (9/1) mixture and after chromatographing on silica gel, elution being carried out with a mixture of cyclohexane and ethyl acetate (9/1), 1.6 g (90%) of the expected product are obtained in the form of a yellow-white powder.

Workup

  1. customobtained
  2. washafter chromatographing on silica gel, elution
  3. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (9/1), 1.6 g (90%) of the expected product
  4. customare obtained in the form of a yellow-white powder

Sources & evidence

ORD record
ord-bf4d315b40c3439a844034f9c0c14fd6
Source dataset
uspto-grants-2013_12
Patent number
US08618301B2

Reaction notes

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