Water → HCID 178454509, compound

HRID 1593668Notes

Reaction equation

HRID 1593668 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([CH:11](CC)C(N)=O)=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](B(O)O)[CH:18]=1.[C:26]([O-])([O-])=O.[Na+].[Na+].[OH2:32].C[N:34]([CH:36]=O)[CH3:35]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:11]2[CH:10]=[C:4]3[C:5]([NH:6][C:7](=[O:32])[CH2:2][CH2:3][CH3:26])=[N:8][NH:9][C:35]3=[N:34][CH:36]=2)[CH:18]=1

Participants

8

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 178449913HCID 178449913, compound

Product 1

HCID 178454509HCID 178454509, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Pd(PPh3)4 (30 mg) was added to a degassed solution of N-(5-bromo-1H-pyrazolo[3,4-b]pyridin-3-yl-butyramide (Description 6; 150 mg, 0.5 mmol), 3-pyridyl boronic acid (95 mg, 0.8 mmol), aq. Na2CO3 (0.75 ml, 2M) in ethanol (0.75 ml) and DMF (1.5 ml). The mixture was stirred at reflux for 12 hours, cooled and then water was added. The resulting solids were filtered and purified by column chromatography (5% MeOH/CHCl3) affording the title compound as a powder.

Workup

  1. temperatureat reflux for 12 hours
  2. temperaturecooled
  3. filtrationThe resulting solids were filtered
  4. custompurified by column chromatography (5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-918184d776ca488fa1dcd1d9513e92cb
Source dataset
uspto-grants-2007_11
Patent number
US07297792B2

Reaction notes

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