Sodium Hydroxide → HCID 118159878, compound

HRID 628406Notes

Reaction equation

HRID 628406 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:20]3[O:21][CH:22]=[CH:23][N:24]=3)[N:10](S(C3C=CC=CC=3)(=O)=O)[C:5]2=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CCO.O>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:20]3[O:21][CH:22]=[CH:23][N:24]=3)[NH:10][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 118159922HCID 118159922, compound

Product 1

HCID 118159878HCID 118159878, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-chloro-2-(1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine (2.09 g, 5.81 mmol, from Step 2) in THF (30 mL) and EtOH (10 mL) was treated with 1.0 M NaOH in water (30 mL, 30 mmol). After stirring for 1 hour, the reaction mixture was diluted with water, and the volatile components were removed in vacuo. The aqueous mixture was extracted with three portions of EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The product was triturated in EtOAc/DCM/MeOH, and the yellow solid was isolated by filtration and air dried. Yield: (0.78 g, 61%).

Workup

  1. customthe volatile components were removed in vacuo
  2. extractionThe aqueous mixture was extracted with three portions of EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was triturated in EtOAc/DCM/MeOH
  8. customthe yellow solid was isolated by filtration and air
  9. customdried

Sources & evidence

ORD record
ord-15ec7bf649354c5d9a05acb72bbef44a
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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