Water → 6-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 1749809Notes

Reaction equation

HRID 1749809 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[Cl-].[CH3:22][Zn+].O>O1CCCC1.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>[CH3:22][C:2]1[N:7]=[C:6]2[N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 862804116-Chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 178477797HCID 178477797, compound

Product 1

HCID 712789696-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

The synthesis was performed with reference to the known literature (US 2006/0148801). A solution of 6-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (0.38 g, 1.2 mmol) in tetrahydrofuran (20 mL) was added with tetrakis(triphenylphosphine)palladium(0) (0.069 g, 0.060 mmol) under an argon atmosphere. Then, the mixture was added dropwise with a 2 M solution of methyl zinc chloride in THF (3.6 mL, 7.2 mmol), and then the mixture was stirred at 60° C. for 48 hours. The reaction mixture was added with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (90:10→50:50)) to obtain 6-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine (0.28 g, 81%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (90:10→50:50))

Sources & evidence

ORD record
ord-0217df0107584c8e92778129f8205e06
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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