Potassium Carbonate → HCID 68814513, compound

HRID 731105Notes

Reaction equation

HRID 731105 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[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:44][C:45]#[N:46]>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][CH2:44][C:45]#[N:46])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[C:9]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68814298HCID 68814298, compound

Product 1

HCID 68814513HCID 68814513, compound

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-phenyl-1H-indol-5-yl)-phenol (0.542 g, 1.163 mmol) was reacted with K2CO3 (0.225 g, 1.628 mmol) and bromoacetonitrile (0.195 g, 1.628 mmol) in acetone (10 ml) to give the product (0.486 g, 0.963 mmol, 83%) as a viscous, yellow oil. 1H NMR (DMSO-d6) δ 4.08 (s, 2H), 5.19 (s, 2H), 5.36 (s, 2H), 6.89 (d, J=7.3 Hz, 2H), 7.10-7.24 (m, 10H), 7.37-7.51 (m, 7H), 7.57 (d, J=8.9 Hz, 2H), 7.63 (s, 1H); [ESI(+)], m/z 505 (M+H)+.

Sources & evidence

ORD record
ord-8816a45837fd431a89e151be053c2428
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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