Sodium Carbonate → 4-[(3,5-difluorobenzyl)amino]-6-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyridine-3-carboxyamide

HRID 2035543Notes

Reaction equation

HRID 2035543 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)[CH:3]=1.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([N:32]2[C:36]3=[N:37][CH:38]=[CH:39][CH:40]=[C:35]3[C:34](B(O)O)=[CH:33]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.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>[F:21][C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([F:20])[CH:17]=1)[CH2:13][NH:12][C:4]1[CH:3]=[C:2]([C:34]2[C:35]3[C:36](=[N:37][CH:38]=[CH:39][CH:40]=3)[N:32]([S:29]([C:26]3[CH:27]=[CH:28][C:23]([CH3:22])=[CH:24][CH:25]=3)(=[O:31])=[O:30])[CH:33]=2)[N:7]=[CH:6][C:5]=1[CH2:8][C:9]([NH2:11])=[O:10]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 45789698(1-Tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)boronic acidHCID 1317309496-Chloro-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide

Product 1

HCID 1317310074-[(3,5-difluorobenzyl)amino]-6-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyridine-3-carboxyamideYield 54.7%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

26 mg of 6-chloro-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of Example 20) was dissolved in 0.5 mL of tetrahydrofuran, to which 33 mg of 1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-boronic acid, 10 mg of tetrakis(triphenylphosphine) palladium (0), and 0.5 mL of 2 mol/L sodium carbonate in water were added, and stirred at 80° C. for 14 hours. To the reaction mixture, water was added, extracted with chloroform, the extract was washed with water, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=20:1) to obtain 25 mg (yield 54%) of the title compound as a white solid.

Workup

  1. additionwere added
  2. extractionextracted with chloroform
  3. washthe extract was washed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-cf4a1ccf73414186a43bb6aad5e9020d
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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