Toluene → HCID 59134891, compound

HRID 1993771Notes

Reaction equation

HRID 1993771 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:16])=[CH:8][C:9]=2[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[CH:4]=[N:3]1.[CH3:17][C:18]1[CH:23]=[C:22]([N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)[CH:21]=[CH:20][C:19]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>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.C(O)C>[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:16])=[CH:8][C:9]=2[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:4]([C:19]2[CH:20]=[CH:21][C:22]([N:24]3[CH:28]=[CH:27][CH:26]=[N:25]3)=[CH:23][C:18]=2[CH3:17])=[N:3]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 59134901HCID 59134901, compoundHCID 68653527HCID 68653527, compound

Product 1

HCID 59134891HCID 59134891, compoundYield 7.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of compound 13a (40 mg, 0.13 mmol), compound 2c (41 mg, 0.20 mmol), tetrakis(triphenylphosphine)palladium(0) (15 mg, 0.013 mmol), aqueous sodium carbonate (0.3 mL of a 2 M solution, 0.6 mmol), toluene (2 mL), and ethanol (2 mL) was heated at 100° C. with stirring for 16 hr in a sealed vial. The mixture was cooled, filtered, and purified by preparative HPLC to afford [1,5-dimethyl-3-(2-methyl-4-pyrazol-1-yl-phenyl)-1H-pyrazolo[4,3-b]pyridin-7-yl]-diethyl-amine (compound 13-1, 3.5 mg).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-59c02cbf2dbd4602ae1601ec150aaf6d
Source dataset
uspto-grants-2010_01
Patent number
US07652035B2

Reaction notes

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