3-furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol → 3-Furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

HRID 1821906Notes

Reaction equation

HRID 1821906 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([C:8]2[NH:16][C:11]3=[CH:12][N:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[OH:7])=[CH:2]1>O1CCCC1.[O-2].[O-2].[Mn+4]>[O:1]1[CH:5]=[CH:4][C:3]([C:6]([C:8]2[NH:16][C:11]3=[CH:12][N:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)=[O:7])=[CH:2]1

Participants

4

Reactant 1

HCID 689822523-furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol

Product 1

HCID 578934443-Furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanoneYield 60.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-Furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (130 mg, 0.61 mmol) was dissolved in tetrahydrofuran (8 mL). Manganese dioxide (530 mg, 6.10=mmol) was added and the reaction mixture was stirred at room temperature for 8 h. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed thoroughly with ethyl acetate. The organic filtrate was concentrated to a tan solid. Drying under vacuum at 40° C. produced 3-furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (78 mg, 60%): mp 232-236° C. dec.; 1H NMR (500 MHz, CD3OD) δ 7.00-7.01 (1H, m), 7.42 (1H, s), 7.71-7.77 (2H, m), 8.16 (1H, d, J=5.6 Hz), 8.53 (1H, d, J=0.8 Hz), 8.85 (1H, s); ESI MS m/z=213 [C12H8N2O2+H]+; HPLC (Method A) >99% (AUC), tR=13.8 min.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washthe filter cake was washed thoroughly with ethyl acetate
  3. concentrationThe organic filtrate was concentrated to a tan solid
  4. customDrying under vacuum at 40° C.

Sources & evidence

ORD record
ord-c1001cc49b184455b2413cbb6e04fe4a
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

Loading…