Potassium Carbonate → [4-(1,3-Dibenzyl-2-methyl-1H-indol-5-yl)-phenoxy]-acetonitrile

HRID 731056Notes

Reaction equation

HRID 731056 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][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:9]1[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:39][C:40]#[N:41]>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][CH2:39][C:40]#[N:41])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:9]1[CH3:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68814952HCID 68814952, compound

Product 1

HCID 68814248[4-(1,3-Dibenzyl-2-methyl-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-(1,3-dibenzyl-2-methyl-1H-indol-5-yl)-phenol (0.164 g, 0.406 mmol) was reacted with K2CO3 (0.073 g, 0.528 mmol) and bromoacetonitrile (0.063 g, 0.528 mmol) in acetone (5 ml) to give the product (0.164 g, 0.371 mmol, 91%) as a pale-yellow, viscous oil. 1H NMR (DMSO-d6) a 2.35 (s, 3H), 4.11 (s, 2H), 5.18 (s, 2H), 5.43 (s, 2H), 6.99 (d, J=7.2 Hz, 2H), 7.09-7.13 (m, 3H), 7.20-7.26 (m, 5H), 7.27-7.30 (m, 3H), 7.41 (d, J=8.4 Hz, 1H), 7.56-7.59 (m, 2H), 7.62 (d, J=1.7 Hz, 1H); [ESI(+)], m/z 443 (M+H)+.

Sources & evidence

ORD record
ord-ea4493b962ad47099b0253947d8d4368
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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