Diisopropylethylamine → 3-{[tert-Butyl(dimethyl)silyl]oxy}-5-ethyl-2-fluorobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of Intermediate 368.3 (440 mg, 1 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.35 mL, 2 mmol) in ACN (30 mL) at −15° C. was added methanesulfonic anhydride (279 mg, 1.6 mmol). The mixture was stirred for 1 h as the temperature was raised to 23° C. 1-(di-(tert-butyloxycarbonyl)amino)-6-aminoisoquinoline (359 mg, 1 mmol) was added as a solid and the mixture stirred 18 h at 50° C. The mixture was concentrated and purified by flash chromatography (0 to 60% EtOAc/hexanes gradient) to afford 394 mg of Intermediate 368.2. 1H NMR (400 MHz, CDCl3) δ ppm 0.04-0.20 (s, 6H) 0.77-1.02 (m, 12H) 1.08-1.37 (s, 18H) 1.09-1.32 (s, 9H) 2.35 (q, J=7.47 Hz, 2H) 3.82 (s, 3H) 5.96-8.33 (m, 13H).

Provenance & Evidence