Sodium Sulfite → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (2-oxo-2-pyridin-3-ylethyl)amide

HRID 751734Notes

Reaction equation

HRID 751734 reaction equation
[OH:1][CH:2]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:3][NH:4][C:5]([C:7]1[NH:16][C:10]2=[CH:11][N:12]=[C:13]([Cl:15])[CH:14]=[C:9]2[CH:8]=1)=[O:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].[O-]S([O-])=O.[Na+].[Na+]>C1COCC1.C([O-])(O)=O.[Na+].O>[O:1]=[C:2]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:3][NH:4][C:5]([C:7]1[NH:16][C:10]2=[CH:11][N:12]=[C:13]([Cl:15])[CH:14]=[C:9]2[CH:8]=1)=[O:6]

Participants

8

Reactant 4

HCID 24437Sodium SulfiteHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 597535745-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (2-hydroxy-2-pyridin-3-yl-ethyl)amide

Product 1

HCID 114157855-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (2-oxo-2-pyridin-3-ylethyl)amide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of racemic 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (2-hydroxy-2-pyridin-3-ylethyl)amide (EXAMPLE 261, 80 mg, 0.253 mmol) in dry THF (20 mL) was added Dess-Martin periodinane (307 mg, 0.724 mmol). After stirring for 4 h at rt alkaline sodium thiosulfate solution was added (5.4 g Na2SO3 dissolved in 20 mL saturated NaHCO3 solution) and the emulsion was vigorously stirred for additional 30 min before further diluted with water (˜150 mL). Extraction with THF (4×50 mL), washing of the combined extracts with saturated sodium hydrogen carbonate (50 mL) and brine (50 mL) gave a solution which was concentrated after drying (MgSO4). Purification of the residue by flash chromatography on silica gel (eluent: DCM/methanol: 90/10) gave the title compound as off-white solid. m/z (ES+)=315.19 [M+H]+; RT=2.65 min.

Workup

  1. additionwas added
  2. extractionExtraction with THF (4×50 mL)
  3. washwashing of the combined extracts with saturated sodium hydrogen carbonate (50 mL) and brine (50 mL)
  4. customgave a solution which
  5. concentrationwas concentrated
  6. dry with materialafter drying (MgSO4)
  7. customPurification of the residue by flash chromatography on silica gel (eluent: DCM/methanol: 90/10)

Sources & evidence

ORD record
ord-4da2e35ac3e24d0e839e488e8c3cf33e
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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