1h-Pyrrolo[2,3-c]pyridine-2-methanol,a-2-pyridinyl- → (pyridin-2-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

HRID 1821897Notes

Reaction equation

HRID 1821897 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:9]1[NH:17][C:12]2=[CH:13][N:14]=[CH:15][CH:16]=[C:11]2[CH:10]=1)[OH:8]>O1CCCC1.[O-2].[O-2].[Mn+4]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[NH:17][C:12]2=[CH:13][N:14]=[CH:15][CH:16]=[C:11]2[CH:10]=1)=[O:8]

Participants

4

Reactant 1

HCID 578934801h-Pyrrolo[2,3-c]pyridine-2-methanol,a-2-pyridinyl-

Product 1

HCID 57893522(pyridin-2-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanoneYield 112%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(Pyridin-2-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (Example 117) (55 mg, 0.24 mmol) was dissolved in tetrahydrofuran (4 mL). Manganese dioxide (210 mg, 2.42 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed thoroughly with tetrahydrofuran. The organic filtrate was concentrated to a yellow solid. Drying under vacuum at 40° C. produced (pyridin-2-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (60 mg, quant.): mp 219-222° C.; 1H NMR (500 MHz, CD3OD) δ7.66-7.76 (2H, m), 7.85 (1H, m), 8.04-8.08 (1H, m), 8.14-8.21 (2H, m), 8.82-8.43 (1H, m), 8.92 (1H, s); ESI MS m/z=224 [C13H9N30+H]+; HPLC (Method A) 95.4% (AUC), tR=13.1 min.

Workup

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

Sources & evidence

ORD record
ord-fde5535486084025993c3a6bb85d0de6
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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