Potassium Carbonate → [4-(1-Benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetonitrile

HRID 731091Notes

Reaction equation

HRID 731091 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:9]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:42][C:43]#[N:44]>CC(C)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:42][C:43]#[N:44])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:9]1[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 688155514-(1-Benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenol

Product 1

HCID 68813877[4-(1-Benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The desired product was prepared using a procedure similar to step 5 of example 3. Thus, 4-(1-benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenol (0.295 g, 0.662 mmol) was reacted with K2CO3 (0.110 g, 0.794 mmol) and bromoacetonitrile (0.095 g, 0.794 mmol) in acetone (10 ml) to give the product (0.265 g, 0.547 mmol, 83%) as a waxy solid, mp 97-99° C. 1H NMR (DMSO-d6) δ 0.72 (t, J=7.0 Hz, 3H), 1.11-1.19 (m, 4H), 1.47-1.57 (m, 2H), 2.65 (t, J=7.6 Hz, 2H), 5.16 (s, 2H), 5.24 (s, 2H), 6.80 (d, J=6.7 Hz, 2H), 7.10-7.18 (m, 5H), 7.32-7.48 (m, 7H), 7.64 (d, J=8.9 Hz, 2H), 7.75 (s, 1H); [ESI(+)], m/z 486 (M+H)+.

Sources & evidence

ORD record
ord-f6b85ea8d9f74868a9f526a3085c7900
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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