1h-Pyrrolo[2,3-c]pyridine-2-methanol,a-phenyl-1-(phenylsulfonyl)- → 1h-Pyrrolo[2,3-c]pyridine,2-benzoyl-1-(phenylsulfonyl)-

HRID 1821824Notes

Reaction equation

HRID 1821824 reaction equation
[C:1]1([CH:7]([C:9]2[N:17]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1.O=[Mn]=O>[C:1]1([C:7]([C:9]2[N:17]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 689818721h-Pyrrolo[2,3-c]pyridine-2-methanol,a-phenyl-1-(phenylsulfonyl)-

Product 1

HCID 689825291h-Pyrrolo[2,3-c]pyridine,2-benzoyl-1-(phenylsulfonyl)-Yield 68%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of phenyl[1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanol (2.6 g, 7.1 mmol) and MnO2 (9.3 g, 110 mmol) in THF (125 mL) was heated to reflux. After 20 h, the reaction mixture was filtered through a pad of diatomaceous earth. The filtrate was concentrated under reduced pressure. Purification by column chromatography (silica gel, CH2Cl2 to 99:1 CH2Cl2/MeOH) gave phenyl[1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanone (1.7 g, 68%) as an off-white solid: mp 145-146° C.; 1H NMR (500 MHz, DMSO-d6) δ7.32 (1H, s), 7.60-7.63 (2H, m), 7.66-7.69 (2H, m), 7.73-7.77 (3H, m), 7.93-7.95 (2H, m), 8.07-8.09 (2H, m), 8.50 (1H, d, J=5.3 Hz), 9.35 (1H, s); ESI MS m/z 363 [C20H14N2O3S+H]+; HPLC (Method A) 99.0% (AUC), tR=18.2 min.

Workup

  1. temperaturewas heated to reflux
  2. filtrationthe reaction mixture was filtered through a pad of diatomaceous earth
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customPurification by column chromatography (silica gel, CH2Cl2 to 99:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-3fcd132925a842279d64e39e4b8b2ba1
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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