Potassium Carbonate → HCID 22474689, compound

HRID 2183584Notes

Reaction equation

HRID 2183584 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6](OS(C(F)(F)F)(=O)=O)[N:5]=[C:4]2[N:21]([CH3:24])[N:22]=[CH:23][C:3]=12.[Cl:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[C:30]([Cl:32])[CH:31]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CCOC(C)=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:28]2[CH:27]=[C:26]([Cl:25])[CH:31]=[C:30]([Cl:32])[CH:29]=2)[N:5]=[C:4]2[N:21]([CH3:24])[N:22]=[CH:23][C:3]=12

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 27343313,5-Dichlorophenylboronic acidHCID 22474688HCID 22474688, compound

Product 1

HCID 22474689HCID 22474689, compoundYield 33%

Reagents, catalysts & solvents 4

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 4-chloro-1-methyl-6-trifluoromethanesulfonyloxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (387 mg, 1 mmol) in THF is treated with tetrakis(triphenyl phosphine) palladium (115 mg, 10 mol %), stirred for 20 min at room temperature, treated sequentially with 3,5-dichlorobenzeneboronic acid (285 mg, 1.5 mmol), 2N K2CO3 (0.7 mL) and benzyl triethyl ammonium chloride (319 mg, 1.4 mmol), heated at reflux temperature for 4 h, cooled to room temperature and diluted with EtOAc. The phases are separated and the organic phase is washed sequentially with water and brine, dried over Na2SO4 and concentrated in vacuo. The resultant residue is chromatographed (silica gel, hexanes:EtOAc, 5:1) to afford the title product as a white solid, 127 mg (33% yield), identified by HNMR analysis.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 4 h
  3. temperaturecooled to room temperature
  4. customThe phases are separated
  5. washthe organic phase is washed sequentially with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is chromatographed (silica gel, hexanes:EtOAc, 5:1)

Sources & evidence

ORD record
ord-fe2c22853053429aaa4d493bef859c7f
Source dataset
uspto-grants-2005_05
Patent number
US06900223B2

Reaction notes

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