Potassium Iodide → HCID 21892157, compound

HRID 720431Notes

Reaction equation

[C:1]([C:9]1[N:13]2[C:14]3[C:19]([CH:20]=[CH:21][C:12]2=[C:11]([C:23]#[N:24])[CH:10]=1)=[C:18]([OH:22])[CH:17]=[CH:16][CH:15]=3)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl[CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[C:1]([C:9]1[N:13]2[C:14]3[C:19]([CH:20]=[CH:21][C:12]2=[C:11]([C:23]#[N:24])[CH:10]=1)=[C:18]([O:22][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)[CH:17]=[CH:16][CH:15]=3)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-benzoyl-3-cyano-6-hydroxy-pyrrolo[1,2-α]quinoline (31 mg, 0.10 mmol), N-(2-chloro-ethyl)-morpholine hydrochloride (25 mg, 0.13 mmol), potassium carbonate (138 mg, 1.0 mmol) and potassium iodide (18 mg, 0.11 mmol) in anhydrous acetone (10 mL) was heated in 60° C. oil bath for 2.5 days. The solvent was evaporated, and the residue was stirred with EtOAc (25 mL) and filtered. The EtOAc filtrate was evaporated and the crude product was purified by chromatography (SiO2, EtOAc/hexanes 50 to 100%) to give a light yellow solid (18 mg, 42%): 1H NMR (CDCl3): 8.21 (d, J=9.6, Hz, 1H), 8.08 (m, 1H), 8.05 (m, 1H), 7.71–7.47 (m, 6H), 7.42 (s, 1H), 6.94 (d, J=7.2 Hz, 1H), 4.33 (t, J=6.0 Hz, 2H), 3.76 (t, J=4.8 Hz, 4H), 2.97 (t, J=6.0 Hz, 2H), 2.65 (t, J=4.5 Hz, 4H).

Workup

customThe solvent was evaporated
filtrationfiltered
customThe EtOAc filtrate was evaporated
customthe crude product was purified by chromatography (SiO2, EtOAc/hexanes 50 to 100%)

Sources & evidence

ORD record: ord-df4b0b70af61464aa238484646873966
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135480B2

Reaction notes

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