Potassium Carbonate → HCID 68814337, compound

HRID 731063Notes

Reaction equation

HRID 731063 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[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:33][C:34]#[N:35]>CC(C)=O>[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH2:33][C:34]#[N:35])=[CH:21][CH:22]=3)[CH:15]=2)[N:10]([CH3:24])[C:9]=1[CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68814801HCID 68814801, compound

Product 1

HCID 68814337HCID 68814337, 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-1,2-dimethyl-1H-indol-5-yl)-phenol (0.159 g, 0.486 mmol) was reacted with K2CO3 (0.087 g, 0.631 mmol) and bromoacetonitrile (0.076 g, 0.631 mmol) in acetone (5 ml) to give the product (0.161 g, 0.439 mmol, 90%) as a white solid, mp 135-138° C. 1H NMR (DMSO-d6) δ 2.40 (s, 3H), 3.68 (s, 3H), 4.07 (s, 2H), 5.18 (s, 2H), 7.08-7.12 (m, 3H), 7.20-7.25 (m, 4H), 7.32 (dd, J=1.8, 8.6 Hz, 1H), 7.41 (d, J=8.4 Hz, 1H), 7.57-7.60 (m, 3H); [ESI(+)], m/z 367 (M+H)+.

Sources & evidence

ORD record
ord-cdec49581586410eb218d161da32a78f
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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