Potassium Carbonate → [4-(9-Benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetonitrile
Reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)=[CH:16][C:15]=2[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:35][C:36]#[N:37]>CC(C)=O>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:35][C:36]#[N:37])=[CH:25][CH:26]=3)=[CH:16][C:15]=2[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
5
Procedure
The desired product was prepared using a procedure similar to step 5 of example 3. Thus, 4-(9-benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenol (0.421 g, 1.191 mmol) was reacted with K2CO3 (0.198 g, 1.429 mmol) and bromoacetonitrile (0.171 g, 1.429 mmol) in acetone to give the product (0.369 g, 0.940 mmol, 79%) as a white solid, mp 149-153° C. 1H NMR (DMSO-d6) δ 1.79-1.86 (m, 4H), 2.63-2.72 (m, 4H), 5.19 (s, 2H), 5.34 (s, 2H), 7.04 (d, J=7.5 Hz, 2H), 7.12 (d, J=7.5 Hz, 2H), 7.22 (t, J=7.2 Hz, 1H), 7.27-7.30 (m, 3H), 7.41 (d, J=8.6 Hz, 1H), 7.62 (s, 1H), 7.65 (d, J=8.6 Hz, 2H); [ESI(+)], m/z 393 (M+H)+.
Sources & evidence
- ORD record
- ord-f3a1785571da42cd9c157c36ea6a2081
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582773B2
Reaction notes
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