Potassium Carbonate → HCID 68814776, compound

HRID 731114Notes

Reaction equation

HRID 731114 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]([O:41][CH3:42])=[O:40]>CC(C)=O>[CH3:42][O:41][C:39](=[O:40])[CH2:38][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[N:10]([CH3:24])[C:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:8]3[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68813921HCID 68813921, compound

Product 1

HCID 68814776HCID 68814776, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The desired product was prepared using a procedure similar to step 1 of example 4. 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 methyl bromoacetate (0.071 g, 0.467 mmol) in acetone (5 ml) to give the product (0.141 g, 0.305 mmol, 85%) as a glass-like solid. 1H NMR (DMSO-d6) δ 3.62 (s, 3H), 3.70 (s, 3H), 4.04 (s, 2H), 4.81 (s, 2H), 6.97 (d, J=8.9 Hz, 2H), 7.07-7.11 (m, 3H), 7.18 (t, J=7.6 Hz, 2H), 7.41-7.57 (m, 10H); [ESI(+)], m/z 462 (M+H)+.

Sources & evidence

ORD record
ord-acc2d10df7e14348b2d9ed0f975afb27
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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