Sodium Hydroxide → HCID 86700288, compound

HRID 879473Notes

Reaction equation

HRID 879473 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[OH-].[Na+]>CC(C)=O.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 867002871H-Pyrrolo[2,3-b]pyridine, 5-bromo-1-[(4-methylphenyl)sulfonyl]-3-(3-pyridinyl)-

Product 1

HCID 86700288HCID 86700288, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5-bromo-3-(pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (662 mg, 1.55 mmol) in acetone (30 mL) and methanol (20 mL) was added 2N NaOH (1.8 mL). The reaction was heated in a 65° C. oil bath for 1 h and then evaporated to near dryness. The crude reaction product was partitioned between EtOAc and 1N NaOH and extracted. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give product that was used for the next step without any further purification. LCMS-ESI+: calc'd for C12H8BrN3: 274.0 (M+H+); found: 274.1 (M+H+).

Workup

  1. customevaporated
  2. customThe crude reaction product
  3. customwas partitioned between EtOAc and 1N NaOH
  4. extractionextracted
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give product that
  9. customwas used for the next step without any further purification

Sources & evidence

ORD record
ord-0b0e6c2af7a2428cb1b8ebd734fa6cdf
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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