2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanol → 2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanone

HRID 1821876Notes

Reaction equation

HRID 1821876 reaction equation
[CH3:1][CH:2]([CH3:14])[CH:3]([C:5]1[NH:13][C:8]2=[CH:9][N:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)[OH:4]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][CH:2]([CH3:14])[C:3]([C:5]1[NH:13][C:8]2=[CH:9][N:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 578934892-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanol

Product 1

HCID 578935262-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanoneYield 88%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanol (Example 78) (75 mg, 0.39 mmol) was dissolved in methylene chloride (10 mL). Manganese dioxide (343 mg, 3.94 mmol) was added and the reaction mixture was stirred for ca. 14 h. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed several times with hot methanol. The filtrate was concentrated to give a white solid. Drying under vacuum produced 2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanone (64 mg, 88%) as a white solid: mp 224-228° C.; 1H NMR (500 MHz, CD3OD) δ1.26 (6H, d, J=7.0 Hz), 3.45-3.62 (1H, m), 7.37 (1H, s), 7.72-7.74 (1H, m), 8.14 (1H, d, J=6.0 Hz), 8.82 (1H, s); ESI MS m/z 189 [C11H12N2O+H]+; HPLC (Method A) 95.4% (AUC), tR=13.7 min.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washthe filter cake was washed several times with hot methanol
  3. concentrationThe filtrate was concentrated
  4. customto give a white solid
  5. customDrying under vacuum

Sources & evidence

ORD record
ord-fa1de021e23d45ccb0124275c7d3b34b
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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