Potassium Carbonate → HCID 68813999, compound

HRID 731070Notes

Reaction equation

HRID 731070 reaction equation
[CH2:1]([N: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)[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](=[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)[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 68814691HCID 68814691, compound

Product 1

HCID 68813999HCID 68813999, 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-6-yl)-phenol (0.291 g, 0.747 mmol) was reacted with K2CO3 (0.124 g, 0.896 mmol) and bromoacetonitrile (0.107 g, 0.896 mmol) in acetone (5 ml) to give the product (0.284 g, 0.663 mmol, 89%) as a white solid, mp 146-150° C. 1H NMR (DMSO-d6) δ 2.20 (s, 3H), 5.15 (s, 2H), 5.36 (s, 2H), 6.82 (d, J=7.0 Hz, 2H), 7.08-7.17 (m, 5H), 7.32-7.47 (m, 4H), 7.45 (t, J=6.7 Hz, 2H), 7.57-7.63 (m, 4H); [ESI(+)], m/z 429 (M+H)+.

Sources & evidence

ORD record
ord-c9053ec8310b4f5592a4f217e595197d
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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