N-[2-(diethylamino)ethyl]-4-fluoro-6-iodoquinoline-2-carboxamide → N-[2-(diethylamino)ethyl]-4-fluoro-6-(tributylstannyl)quinoline-2-carboxamide
Reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:18]=[C:17]([F:19])[C:16]2[C:11](=[CH:12][CH:13]=[C:14](I)[CH:15]=2)[N:10]=1)=[O:8])[CH3:2].C(N(CC)CCN[C:29]([C:31]1[CH:32]=[C:33]([Sn:42](CCCC)([CH2:47][CH2:48][CH2:49][CH3:50])[CH2:43][CH2:44][CH2:45][CH3:46])C=C2C=1N=CC=C2F)=O)C>>[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:18]=[C:17]([F:19])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Sn:42]([CH2:43][CH2:44][CH2:45][CH3:46])([CH2:47][CH2:48][CH2:49][CH3:50])[CH2:33][CH2:32][CH2:31][CH3:29])[CH:15]=2)[N:10]=1)=[O:8])[CH3:2]Participants
3
Procedure
This compound was prepared, starting from compound 106 (206 mg, 0.50 mmol), according to the procedure developed for compound 112. The purification was performed using column chromatography (Al2O3, cyclohexane/AcOEt, 5/5, v/v) to give compound 113 (165 mg, 0.29 mmol) as an orange oil. Yield 57%; Rf (Al2O3, cyclohexane/AcOEt, 5/5, v/v) 0.73; IR (CCl4) ν 1521, 1684, 2929, 2962 cm−1; 1H NMR (200 MHz, CDCl3) δ 0.88 (t, 9H, J=7.0 Hz), 1.10 (t, 6H, J=7.1 Hz), 1.17 (m, 6H), 1.33 (m, 6H), 1.55 (m, 6H), 2.64 (q, 4H, J=7.1 Hz), 2.74 (t, 2H, J=6.3 Hz), 3.59 (q, 2H, J=6.3 Hz), 7.88 (d, 1H, J=8.3 Hz), 7.94 (d, 1H, 3JH-F=10.4 Hz), 8.04 (dd, 1H, J=1.4, 8.3 Hz), 8.20 (d, 1H, 3J119Sn/117Sn-H=40.8 Hz), 8.61 (m, 1H); ESI-MS m/z 580.2 [M+H]+.
Workup
- customThis compound was prepared
- customThe purification
Sources & evidence
- ORD record
- ord-5b7ba8c6f3a34af89b38f7d0cc343d7f
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09125937B2
Reaction notes
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