Bromoacetonitrile → HCID 68958685, compound
Reaction equation
[CH2:1]([C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]=1[C:15]1[CH:24]=[CH:23][C:22]([O:25]C)=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:27]([C:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[O:34][C:33]=1[C:41]1[CH:50]=[CH:49][C:48]([OH:51])=[C:47]2[C:42]=1[CH:43]=[CH:44][CH:45]=[N:46]2)[CH2:28][CH2:29][CH2:30][CH3:31].Br[CH2:53][C:54]#[N:55]>>[CH2:1]([C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]=1[C:15]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:27]([C:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[O:34][C:33]=1[C:41]1[CH:50]=[CH:49][C:48]([O:51][CH2:53][C:54]#[N:55])=[C:47]2[C:42]=1[CH:43]=[CH:44][CH:45]=[N:46]2)[CH2:28][CH2:29][CH2:30][CH3:31]Participants
Procedure
5-(3-Pentyl-1-benzofuran-2-yl)-8-hydroxy-quinoline was prepared as a solid (0.113 g, 99%) from 5-(3-pentyl-1-benzofuran-2-yl)-8-methoxy-quinoline according to the procedure described in the first part of Step 4 of Example 2. Mass spectrum (+ESI, [M+H)+) m/z 332. Reaction of 5-(3-Pentyl-1-benzofuran-2-yl)-8-hydroxy-quinoline with bromoacetonitrile according to the procedure described in Step 2 of Example 1 afforded the title compound as a solid (0.059 g, 48%). Mass spectrum (+ESI, [M+H)+) m/z 371. 1H NMR (500 MHz, DMSO-d6): δ 8.94-9.02 (m, 1H), 8.20 (d, 1H, J=9.5 Hz), 7.72-7.83 (m, 2H), 7.60-7.70 (m, 2H), 7.53 (d, 1H, J=8.6 Hz), 7.28-7.42 (m, 2H), 5.52 (s, 2H), 2.68 (t, 2H, J=7.4 Hz), 1.50-1.67 (m, 2H), 1.03-1.26 (m, 4H), and 0.67 ppm (t, 3H, J=7.0 Hz).
Sources & evidence
- ORD record
- ord-4986a0f7d85a4196a8e8c6511efd1448
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07446201B2
Reaction notes
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