Diisopropylethylamine → HCID 18617738, compound

Participants

Reaction Steps

To a suspension of 5-(2-amino-ethyl)3-cyano-indole (reference example 2) (925 mg, 5 mmol) in CH2Cl2/THF (20 mL, 1/1) is added N,N-diisopropylethylamine (869 mL, 5 mmol) followed by allyl-1-benzotriazolyl carbonate (1.096 g, 5 mmol). The resulting mixture is stirred for 25 minutes then concentrated. The residue is purified by flash chromatography (eluting with 7% MeOH in CH2Cl2) to give 1.27 g of product as a white solid. 1H NMR (CDCl3) d 2.92 (t, J=7 Hz, 2H), 3.50 (q, J=7 Hz, 2H), 4.53 (d, J=5 Hz, 2H), 4.79 (bs, 1H), 5.18 (d, J=10 Hz, 1H), 5.26 (d, J=17 Hz, 1H), 5.87 (m, 1H), 7.10 (dd, J=8,1 Hz, 1H), 7.34 (d, J=8 Hz, 1H), 7.54 (s, 1H), 7.67 (d, J=1 Hz, 1H), 9.08 (bs, 1H). MS (EI) m/z 269 (M+).

Provenance & Evidence