2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → HCID 67332161, compound

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Reaction Conditions

Reaction Steps

To the solution of tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate (500 mg, 1.407 mmol) in MeCN (15 mL) was added resin-supported BEMP (786 mg, 1.547 mmol) and 3-bromo-5-(bromomethyl)benzonitrile (503 mg, 1.829 mmol). The mixture was heated in a microwave synthesizer at 90° C. for 3 hours. The reaction mixture was filtered, rinsed alternatively with dichloromethane and methanol. The filtrate was concentrated to give a reddish orange residue, which was purified by silica chromatography to obtain a white powder (616 mg, 80% yield). 1H NMR (500 MHz, CDCl3) δ 7.69 (d, J=8.6 Hz, 2H), 7.57-7.52 (m, 2H), 7.49 (s, 1H), 6.85 (d, J=9.3 Hz, 1H), 4.49 (s, 2H), 3.82 (s, 2H), 2.81 (t, J=6.7 Hz, 2H), 1.84 (t, J=6.7 Hz, 2H), 1.36 (s, 9H), 1.36 (s, 6H). LRMS [ESI, MH+] m/z calcd for C25H30BrN2O5S 549.11, found 549.1.

Provenance & Evidence