Nitrogen → HCID 66874246, compound

Participants

Reaction Steps

8.5 g 9-(3-bromophenyl)-carbazole from step (1b) above, 0.12 g Pd2DBA3 0.11 g dicyclohexylphosphinebiphenyl and 50 mL dioxane were stirred in a glove box (N2). 9.2 g LiN[Si(Me)3]2 and a further 10 mL dioxane were added and the reaction brought to reflux overnight. The reaction was cooled and remove from the glove and water was added slowly. The pH of the aqueous layer was brought to 9 with carbonate and then the mixture was extracted with DCM. The DCM layer was separated and dried over magnesium sulfate then chromatographed on silica eluting with 1:1 ethylacetate:hexanes. The product elutes as a tan solution which on evaporation and addition of methanol produces a tan colored crystalline solid in ˜90% yield. 1-H nmr shows it to be the desired aniline product.

Provenance & Evidence