2-Bromomethylnaphthalene → HCID 67283244, compound

Participants

Reaction Conditions

Reaction Steps

7-Chloro-1-(4-methoxybenzyl)-5-(1H-pyrazol-4-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one (163 mg) was dissolved in THF (3 mL) and the solution was cooled to −78° C. A solution of KOtBu in THF (1 M, 1.1 mL, 2.6 eq) was then added dropwise and the anion was stirred for 10 minutes. 2-Bromomethyl naphthalene (123 mg, 1.3 eq) was then added and the reaction was allowed to warm to room temperature where it was held for 2 hours. The reaction was then quenched with saturated aqueous ammonium chloride and the crude product was partitioned between water and EtOAc. The organic fraction was washed with brine, then dried over sodium sulfate, and concentrated onto silica gel then purified by flash chromatography (gradient: 3:1 hexanes:EtOAc to EtOAc) delivering the product as a solid (106 mg, 48% yield). MS (ES+) m/z 521.2 (M+1).

Provenance & Evidence