Potassium Carbonate → HCID 68815118, compound

HRID 731030Notes

Reaction equation

HRID 731030 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[C:4]([CH3:18])=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:32][C:33]#[N:34]>CC(C)=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:32][C:33]#[N:34])=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[C:4]([CH3:18])=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68815835HCID 68815835, compound

Product 1

HCID 68815118HCID 68815118, compoundYield 91.2%

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-dimethyl-2-phenyl-1H-indol-5-yl)-phenol (0.353 g, 1.126 mmol) was reacted with K2CO3 (0.189 g, 1.352 mmol) and bromoacetonitrile (0.162 g, 1.352 mmol) in acetone (15 ml) to give the desired product (0.362 g, 1.027 mmol, 91%) as a white solid, mp 177-179° C. 1H NMR (DMSO-d6) δ 2.25 (s, 3H), 3.61 (s, 3H), 5.21 (s, 2H), 7.15 (d, J=8.7 Hz, 2H), 7.45-7.52 (m, 5H), 7.55 (t, J=7.5 Hz, 2H), 7.72 (d, J=8.9 Hz, 2H), 7.78 (s, 1H); [EI], m/z 352 (M)+.

Workup

  1. customThe desired product was prepared

Sources & evidence

ORD record
ord-7bef53355af443e285d3ec648f3f2fe0
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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