Cesium carbonate → HCID 70312045, compound

HRID 1918195Notes

Reaction equation

HRID 1918195 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.[OH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>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].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:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[CH2:19][OH:18])[CH:7]=[CH:6][N:5]3[N:8]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 43742622-(Hydroxymethyl)phenylboronic AcidHCID 67254097HCID 67254097, compound

Product 1

HCID 70312045HCID 70312045, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

The procedure described in Example 3 is followed. Starting from 0.3 g (0.98 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, 0.18 mg (1.18 mmol) of 2-(hydroxymethyl)phenylboronic acid, 0.975 g (2.99 mmol) of caesium carbonate, 0.085 g (0.10 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and 5 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 (7/3), 0.303 g (92%) of the expected product is obtained in the form of a white powder.

Workup

  1. customobtained
  2. washafter chromatographing on silica gel, elution
  3. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (7/3)

Sources & evidence

ORD record
ord-8d7b47799ac142279c9c8562ce068096
Source dataset
uspto-grants-2013_12
Patent number
US08618301B2

Reaction notes

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