HCID 57757929, compound → HCID 57758159, compound

Participants

Reaction Steps

A suspension of PtO2 (16 mg, 0.070 mmol) in acetic acid (0.5 ml) was added to a suspension of ethyl (2E)-3-[4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]acrylate (144 mg, 0.408 mmol) in acetic acid (2 ml) under N2 atmosphere. The flask was evacuated and refilled with hydrogen gas (3×) and the reaction proceeded under a hydrogen atmosphere (1 atm) for 1 d. Additional PtO2 (50 mg, 0.22 mmol) in acetic acid (0.5 ml) was added and the reaction proceeded under H2 atmosphere for an additional 1 d. The reaction was filtered through a Celite pad and washed with MeOH. It was evaporated to dryness, diluted with EtOAc and washed with aqueous Na2CO3. The aqueous layer was back extracted with EtOAc (2×). Organic was dried (Na2SO4), filtered, and evaporated to dryness to afford the above compound as a yellow solid (120 mg, yield 90%). 1H-NMR (CD3OD) δ 7.70 (s, 1H), 7.47 (s, 1H), 7.12 (d, J=8.3 Hz, 2H), 6.84 (d, J=8.3 Hz, 2H), 4.06 (q, J=7.8 Hz, 2H), 2.82 (t, J=7.8 Hz, 2H), 2.48 (t, J=7.7 Hz, 2H), 1.18(t, J=7.8 Hz, 3H); MS [M+H]+=326; LCMS RT=1.20 min.

Provenance & Evidence