HCID 22179999, compound → HCID 22180051, compound

Participants

Reaction Steps

To a solution of 3-benzyl-7-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-2-carbaldehyde (1.50 g, 5.21 mmol) in anhydrous CH2Cl2 (20 mL) at −76° C. under nitrogen was added dropwise cyclopropylmagnesium bromide (Boulder Scientific, 0.76 M, 20 mL, 15.2 mmol) in THF over 15 min. The reaction mixture was stirred at −70–50° C. for 1 h, quenched with aq. NH4Cl and 1 N HCl, and extracted with EtOAc (3×70 mL). The EtOAc layers were dried and concentrated. Purification of the crude product by flash column chromatography (SiO2, EtOAc/hexane 1.5:8.5 to 1:4) gave the title compound as a pale oil (1.2 g, 70%): 1H NMR (CDCl3) δ 7.24 (m, 2H), 7.19 (m, 1H), 7.09 (m, 2H), 7.00 (d, 1H, J=4.4 Hz), 6.44 (d, 1H, J=4.4 Hz), 5.33 (q, 2H, AB), 4.10 (t, 1H, J=7.15 Hz), 2.62 (d, 1H, J=7.7 Hz), 1.40 (m, 1H), 0.51 (m, 2H), 0.32 (m, 1H), 0.14 (m, 1H); 13C NMR (CDCl3) δ 154.3, 150.5, 136.1, 129.0, 127.8, 126.2, 117.8, 117.3, 110.2, 108.6, 72.76, 44.6, 15.5, 3.0; MS (ESI+) 330.10 (M++H), 352.13, 354.13 (M++Na).

Provenance & Evidence