Sodium Hydroxide → 2-bromo-5-chloro-1H-pyrrolo[3,2-b]pyridine

HRID 628363Notes

Reaction equation

HRID 628363 reaction equation
[Br:1][C:2]1[N:10](S(C2C=CC=CC=2)(=O)=O)[C:9]2[C:4](=[N:5][C:6]([Cl:20])=[CH:7][CH:8]=2)[CH:3]=1.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[NH:10][C:9]2[C:4](=[N:5][C:6]([Cl:20])=[CH:7][CH:8]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1181595562-Bromo-5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 1181597982-bromo-5-chloro-1H-pyrrolo[3,2-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine (20.7 g, 44.6 mmol, prepared as in Example 62, Step 1, but isolated as the free base) in THF (300 mL) was stirred with 1N NaOH (300 mL, 300 mmol) overnight. The reaction mixture was extracted with EtOAc three times. The combined extracts were dried over sodium sulfate, filtered, and concentrated to afford 2-bromo-5-chloro-1H-pyrrolo[3,2-b]pyridine in theoretical yield. LCMS (M+H)+: 233.0 (most abundant).

Workup

  1. extractionThe reaction mixture was extracted with EtOAc three times
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a168b2afd33049fc9039f7a008b3a013
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

Loading…