1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanol → 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone

HRID 1821867Notes

Reaction equation

HRID 1821867 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[CH:10]([OH:12])[CH3:11]>C1COCC1.[O-2].[O-2].[Mn+4]>[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10](=[O:12])[CH3:11]

Participants

4

Reactant 1

HCID 578934541-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanol

Product 1

HCID 552679001-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanol (Example 68) (0.65 g, 4.0 mmol) in THF (80 mL) was added manganese dioxide (4.18 g, 48 mmol). After stirring 2 h at room temperature, TLC analysis indicated that the reaction was completed. The reaction mixture was filtered through diatomaceous earth and rinsed with EtOAc. The filtrate was concentrated and triturated with Et2O to provide 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone as an off-white solid: mp 236-242° C. dec.; 1H NMR (300 MHz, CD3OD) δ2.63 (3H, s), 7.34 (1H, s), 7.70-7.73 (1H, m), 8.13 (1H, d, J=5.7 Hz), 8.80 (1H, s); ESI MS m/z 161 [C9H8N2O+H]+; HPLC (Method A) 92.7% (AUC), tR=7.75 min.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washrinsed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. customtriturated with Et2O

Sources & evidence

ORD record
ord-82c0c50ccd6e4d9a894121c27b5cd972
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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