Potassium Carbonate → HCID 68814808, compound

HRID 731077Notes

Reaction equation

HRID 731077 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:24])=[C:9]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:38][C:39]#[N:40]>CC(C)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:38][C:39]#[N:40])=[CH:19][CH:18]=3)[CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:24])=[C:9]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68815056HCID 68815056, compound

Product 1

HCID 68814808HCID 68814808, 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-benzyl-3-methyl-2-phenyl-1H-indol-4-yl)-phenol (0.260 g, 0.668 mmol) was reacted with K2CO3 (0.111 g, 0.802 mmol) and bromoacetonitrile (0.096 g, 0.802 mmol) in acetone (5 ml) to give the product (0.271 g, 0.633 mmol, 95%) as a viscous oil. 1H NMR (DMSO-d6) δ 1.72 (s, 3H), 5.22 (s, 2H), 5.33 (s, 2H), 6.85-6.89 (m, 3H), 7.11-7.14 (m, 3H), 7.17 (t, J=7.2 Hz, 1H), 7.22 (t, J=7.0 Hz, 2H), 7.33-7.35 (m, 3H), 7.39-7.47 (m, 5H); [ESI(+)], m/z 429 (M+H)+.

Sources & evidence

ORD record
ord-2c26eaf8582245bbb84ad4bbe4307153
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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