Pyrrolidine → (3E)-3-[1-(1H-indazol-6-yl)ethylidene]-1H-indol-2-one

HRID 1615259Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].N1CCCC1.[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25](=O)[CH3:26])[CH:23]=2)[CH:18]=[N:17]1>C1(C)C=CC=CC=1>[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22](/[C:25](=[C:3]3/[C:2](=[O:10])[NH:1][C:9]4[C:4]/3=[CH:5][CH:6]=[CH:7][CH:8]=4)/[CH3:26])[CH:23]=2)[CH:18]=[N:17]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of oxindole (16 mg, 0.12 mmol), pyrrolidine (10 μL, 0.12 mmol) and 1-(1H-indazol-6-yl)ethanone (20 mg, 0.12 mmol) in toluene was refluxed in a Dean-Stark trap for 2 h. The solution was then stirred at 50° C. for 72 h. Two equivalents of pyrrolidine were added and the solution was heated to reflux for 48 h. The solution was concentrated and the red residue was purified by preparatory HPLC to give the title compound as an orange solid (5 mg, 16%). 1H NMR (400 MHz, CDCl3) δ 8.13 (s, 1H), 7.78 (s, 1H), 7.70 (d, 1H, J=8.5 Hz), 7.34 (d, 1H, J=8.5 Hz), 7.03 (t, 1H, J=7.6 Hz), 6.81 (d, 1H, J=7.7 Hz), 6.50 (t, 1H, J=7.6 Hz), 6.05 (d, 1H, J=7.7 Hz), 2.82 (s, 3H); MS ESI [M+H]+, calcd for [C17H13N3O+H]+ 276.1; found m/z 276.0.

Workup

temperaturethe solution was heated
temperatureto reflux for 48 h
concentrationThe solution was concentrated
customthe red residue was purified by preparatory HPLC

Sources & evidence

ORD record: ord-495c4388490e4472b86ce6f19a21c3db
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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