Methanol → 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carbaldehyde

HRID 628290Notes

Reaction equation

HRID 628290 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([CH:20]=[O:21])[N:10](S(C3C=CC=CC=3)(=O)=O)[C:5]2=[CH:4][CH:3]=1.[OH-].[Na+].CO.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([CH:20]=[O:21])[NH:10][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 1181598205-chloro-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine-2-carbaldehyde

Product 1

HCID 1181597355-chloro-1H-pyrrolo[3,2-b]pyridine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine-2-carbaldehyde (0.42 g, 1.3 mmol, prepared in Step 1) in THF (10 mL) was added to a mixture of 2.8 M NaOH (12 mL, 34 mmol) and MeOH (10 mL) at 0° C. After 40 minutes, the reaction was allowed to come to room temperature and stir for 30 minutes. Saturated NH4Cl was added and was extracted twice with DCM. The extracts were washed with water and then with brine, dried over sodium sulfate, filtered and concentrated. Flash chromatography, eluting with a gradient from 0-30% EtOAc in hexanes afforded product as a white solid (0.19 g, 80%).

Workup

  1. customto come to room temperature
  2. extractionwas extracted twice with DCM
  3. washThe extracts were washed with water
  4. dry with materialwith brine, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washFlash chromatography, eluting with a gradient from 0-30% EtOAc in hexanes afforded product as a white solid (0.19 g, 80%)

Sources & evidence

ORD record
ord-f337673de2bd4d25b9da39ecdd69d682
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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