1,10-Phenanthroline → HCID 68095389, compound

HRID 1502316Notes

Reaction equation

I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.N1C2C(=CC=C3C=2N=CC=C3)[CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-:33].[Cs+].[Cs+]>C(O)(C)C.ClCCl.[Cu]I>[CH:20]([O:33][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])[N:8]=[CH:9]2)=[CH:4][CH:3]=1)([CH3:21])[CH3:19]

Participants

Conditions

Temperature: 210 °C

Procedure

A mixture of N-(7-iodoisoquinolin-3-yl)cyclopropanecarboxamide (338 mg, 1.0 mmol), 1,10-phenanthroline (180 mg, 1.0 mmol), copper(I) iodide (190 mg, 1.0 mmol) and cesium carbonate (422.5 mg, 1.3 mmol) in isopropanol (25 mL) were stirred at 210° C. for 5 hours under nitrogen in a sealed stainless container. After being cooled to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite and filter cake was washed with dichloromethane. The combined filtrates were concentrated and purified by prep-HPLC to give product (18.9 mg, 26%). LCMS (ESI): RT (min)=0.967, M+H+=271.1, method=A. 1H NMR (400 MHz, CDCl3) δ 8.80 (s, 1H), 8.45 (s, 1H), 8.28 (s, 1H), 7.68 (d, J=9.2 Hz, 1H), 8.02 (t, J=0.8 Hz, 1H), 7.84 (d, J=8.8 Hz, 1H), 7.53 (dd, J=1.6, 8.4 Hz, 1H), 7.38-7.31 (m, 5H), 2.09-1.99 (m, 1H).

Workup

temperatureAfter being cooled to room temperature
filtrationfiltered through a pad of Celite
filtrationfilter cake
washwas washed with dichloromethane
concentrationThe combined filtrates were concentrated
custompurified by prep-HPLC

Sources & evidence

ORD record: ord-8253ff301ea74861bfdad1b7bc30b87c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206175B2

Reaction notes

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