1-Bromooctane → HCID 49780539, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][CH2:14]CCCC)[CH:6]=[C:5]2[CH2:19][C:20]([NH2:22])=[O:21].Br[CH2:24]CCCCCCC>>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH:12]=[C:13]([CH3:14])[CH3:24])[CH:6]=[C:5]2[CH2:19][C:20]([NH2:22])=[O:21]Participants
Procedure
2-(5-Fluoro-1-octyl-1H-indol-3-yl)acetamide) (1-8). The reaction between Amide A-2 and bromooctane can be carried out as described by Na, Y. M.; Le Borgne, M.; Pagniez, F.; Le Baut, G.; Le Pape, P. Synthesis and antifungal activity of new 1-halogenobenzyl-3-imidazolylmethylindole derivatives. Eur J Med Chem 2003, 38, 75-87. Yield: 70%; 1H NMR (300 MHz, CDCl3): δ7.26-7.18 (m, 2 H), 7.09 (s, 1 H), 6.97 (dt, J1=9 Hz, J2=2.4 Hz, 1 H), 5.73 (br. s, 2 H), 4.06 (t, J=7.2 Hz, 2 H), 3.65 (s, 2 H), 1.83 (t, J=6.3 Hz, 2 H), 1.29-1.25 (m, 10 H), 0.86 (t, J=6.3 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 174.10, 159.39, 156.27, 139.66, 133.03, 128.67, 127.68, 127.55, 110.66, 117.23, 103.88, 46.63, 32.81, 31.70, 30.17, 29.09 (2C), 26.94, 22.55, 14.02; MS (APCI): m/z 305.5 [M+H]+
Sources & evidence
- ORD record
- ord-d93939f885c94188be23abb81a431da3
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08742100B2
Reaction notes
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