Benzaldehyde → HCID 86703964, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 2A) (200 mg, 0.47 mmoles) in THF (2.6 mL) in a screw-capped vial under argon at −78° C. is added 2.3M nBuLi (0.44 mL, 0.94 mmole). The reaction mixture is stirred at −78° C. for 30 min. Benzaldehyde (96 μL, 1.03 mmole) is added. The reaction mixture is allowed to reach room temperature. Water and a NaHCO3 saturated solution are added, and the aqueous phase is extracted three times with AcOEt. The organic phase is washed with water, brine, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (CH2Cl2:MeOH:NH4OH) as eluent with a gradient from (98:2:0.2) to (95:5:0.5). The residue (130 mg, 0.285 mmole) is dissolved in 1,4-dioxane (1.4 mL) and barium manganate (73 mg, 0.285 mmole) as well as MnO2 (100 mg, 1.14 mmole) are added. The reaction mixture is heated at 80° C. for 24 h. The reaction mixture is filtered over celite, cake washed with MeOH. The solvents are removed under reduced pressure. The residue is purified by silica gel chromatography using (CH2Cl2:MeOH:NH4OH) as eluent with a gradient from (98:2:0.2) to (96.5:3.5:0.35) to give {4-[4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-phenyl}-phenyl-methanone.

Provenance & Evidence