Sodium Carbonate → 2-methyl-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 85075Notes

Reaction equation

HRID 85075 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[CH:12]=[C:11]2[CH3:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=2)[CH2:24][CH2:23]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:20][C:11]1[N:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[C:14]2=[N:15][CH:16]=[C:17]([C:32]3[CH:31]=[CH:30][C:29]([CH2:28][N:25]4[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]4)=[CH:34][CH:33]=3)[CH:18]=[C:13]2[CH:12]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 454965984-((4-Methylpiperazin-1-yl)methyl)phenylboronic acidHCID 509877345-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 866916602-methyl-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 74.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1-Benzenesulfonyl-5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (378 mg, 1.076 mmole) and 4-((4-methylpiperazin-1-yl)methyl)phenylboronic acid (303 mg, 1.29 mmole) are dissolved in acetonitrile (10 mL) and treated with 10 mL 1 M sodium carbonate solution. To this is added 40 mg of PdCl2(PPh3)2 catalyst, and the mixture is irradiated for 5 minutes at 150 degrees in a Biotage microwave reactor. After cooling, the reaction mixture is diluted with water and extracted with ethyl acetate, dried, and concentrated. MPLC silica gel chromotagraphy 5-20% MeOH in dichloromethane gradient elution, provided 367 mg of the title compound as a solid.

Workup

  1. customthe mixture is irradiated for 5 minutes at 150 degrees in a Biotage microwave reactor
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated
  6. washMPLC silica gel chromotagraphy 5-20% MeOH in dichloromethane gradient elution

Sources & evidence

ORD record
ord-c6c47da688594eaea5cf625797af4a36
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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