6-Chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine → 6-Methyl-1H-pyrrolo[2,3-b]pyridine

HRID 273328Notes

Reaction equation

HRID 273328 reaction equation
[Cl-].[CH3:2][Zn+].Cl[C:5]1[N:10]=[C:9]2[N:11](S(C3C=CC=CC=3)(=O)=O)[CH:12]=[CH:13][C:8]2=[CH:7][CH:6]=1>C1COCC1.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>[CH3:2][C:5]1[N:10]=[C:9]2[C:8]([CH:13]=[CH:12][NH:11]2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 497590336-Chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 178477797HCID 178477797, compound

Product 1

HCID 114577166-Methyl-1H-pyrrolo[2,3-b]pyridineYield 88%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of methylzinc chloride in THF (2 M) (9 mL, 12 mmol) was added to 6-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.600 g, 2.05 mmol) and Pd(PPh3)4 (0.095 g, 0.08 mmol) in THF (30 mL). The mixture was refluxed for 40 h, cooled to 0° C., quenched with water and extracted with Et2O. The organic layer was concentrated and the residue was purified over a silica gel column eluting with EtOAc/hexane (1:5) to give N-protected 6-methyl-7-azaindole (0.495 g, 88%).

Workup

  1. temperatureThe mixture was refluxed for 40 h
  2. customquenched with water
  3. extractionextracted with Et2O
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified over a silica gel column
  6. washeluting with EtOAc/hexane (1:5)

Sources & evidence

ORD record
ord-e565e8d0101240769f247e2833515134
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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