Potassium Carbonate → HCID 68814796, compound

HRID 731112Notes

Reaction equation

HRID 731112 reaction equation
[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH:15]=2)[N: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]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:38][C:39]#[N:40])=[CH:19][CH:18]=3)[CH:15]=2)[N: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 68813921HCID 68813921, compound

Product 1

HCID 68814796HCID 68814796, 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-(3-benzyl-1-methyl-2-phenyl-1H-indol-5-yl)-phenol (0.140 g, 0.359 mmol) was reacted with K2CO3 (0.065 g, 0.467 mmol) and bromoacetonitrile (0.056 g, 0.467 mmol) in acetone (5 ml) to give the product (0.141 g, 0.329 mmol, 92%) as a glass-like solid. 1H NMR (DMSO-d6) δ 3.62 (s, 3H), 4.04 (s, 2H), 5.18 (s, 2H), 7.07-7.13 (m, 5H), 7.18 (t, J=7.5 Hz, 2H), 7.44-7.49 (m, 4H), 7.52-7.55 (m, 3H), 7.57-7.60 (m, 3H); [ESI(+)], m/z 429 (M+H)+.

Sources & evidence

ORD record
ord-27b3656173ad4d0a9b5e2f4277ac98db
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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