Ammonia → Ammonium Hydroxide

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-chloro-2-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 78A) (35 mg, 0.08 mmole) in THF (1 mL) in a screw-capped vial under argon are added 1M solution of K2CO3 (0.4 ml, 0.4 mmole), PdCl2(dppf)2 (3.5 mg) and benzeneboronic acid (13 mg, 0.104 mmole). The reaction mixture is heated at 100° C. overnight. Water is added to the reaction mixture and pH adjusted to 9-10 by adding concentrated ammonia solution. The aqueous phase is extracted three times with CH2Cl2. The organic phase is dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is pre-purified by silica gel chromatography using (CH2Cl2:MeOH) (100:0) to (90:10) then (CH2Cl2:MeOH:NH4OH) (9:1:0.1) to give 8-chloro-4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene. [M+H]+=408.2 and 410.0 35Cl/37Cl.

Provenance & Evidence