Potassium Carbonate → HCID 68813959, compound

HRID 731084Notes

Reaction equation

HRID 731084 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[CH:7]=[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](=[C:6]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:32][C:33]#[N:34])=[CH:13][CH:12]=3)[CH:7]=[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 68813887HCID 68813887, compound

Product 1

HCID 68813959HCID 68813959, 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-dimethyl-2-phenyl-1H-indol-4-yl)-phenol (0.300 g, 0.957 mmol) was reacted with K2CO3 (0.159 g, 1.148 mmol) and bromoacetonitrile (0.134 g, 1.148 mmol) in acetone (5 ml) to give the product (0.311 g, 0.882 mmol, 92%) as a viscous oil. 1H NMR (DMSO-d6) δ 1.66 (s, 3H), 3.55 (s, 3H), 5.17 (s, 2H), 6.82 (dd, J=0.9, 7.2 Hz, 1H), 7.08 (d, J=8.9 Hz, 2H), 7.16 (t, J=7.2 Hz, 1H), 7.34-7.43 (m, 6H), 7.48 (t, J=7.0 Hz, 2H); [ESI(+)], m/z 353 (M+H)+.

Sources & evidence

ORD record
ord-30d9bf0b6b504638ab9faa97e9a5944e
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

Loading…