Sodium Hydroxide → HCID 57893482, compound

Participants

Reaction Steps

[1-(Phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-2-yl](pyridin-4-yl)methanol (Reference Example 22, 217 mg, 0.59 mmol) was dissolved in ethanol (10 mL). A 10% solution of sodium hydroxide (6 mL) was added and the reaction mixture was refluxed for 4.5 hours and then stirred at ambient temperature for the weekend. The solvent was removed under vacuum. The residue was taken up in ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated to give (pyridin-4-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (air-oxidation product) (86 mg, 65%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.26 (1H, s), 7.75-7.77 (1H, m), 7.90-7.92 (2H, m), 8.18 (1H, d, J=5.6 Hz), 8.81-8.83 (2H, m), 8.90 (1H, s); ESI MS m/z=224 [C13H9N3O+H]+; HPLC (Method A) >99% (AUC), tR=7.6 min.

Provenance & Evidence