Potassium Carbonate → HCID 68814804, compound

HRID 731107Notes

Reaction equation

HRID 731107 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:9]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:44][C:45]([O:47][CH3:48])=[O:46]>CC(C)=O>[CH3:48][O:47][C:45](=[O:46])[CH2:44][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:10]3[CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68814298HCID 68814298, compound

Product 1

HCID 68814804HCID 68814804, 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-(1,3-dibenzyl-2-phenyl-1H-indol-5-yl)-phenol (0.541 g, 1.163 mmol) was reacted with K2CO3 (0.225 g, 1.628 mmol) and methyl bromoacetate (0.249 g, 1.628 mmol) in acetone (10 ml) to give the product (0.525 g, 0.976 mmol, 84%) as a solid. 1H NMR (DMSO-d6) δ 3.66 (s, 3H), 4.03 (s, 2H), 4.77 (s, 2H), 5.30 (s, 2H), 6.84 (d, J=6.8 Hz, 2H), 6.93 (d, J=8.8 Hz, 2H), 7.04-7.20 (m, 8H), 7.30 (dd, J=1.7, 8.5 Hz, 1H), 7.35-7.47 (m, 8H), 7.54 (d, J=1.2 Hz, 1H); [ESI(+)], m/z 538 (M+H)+.

Sources & evidence

ORD record
ord-dd1d51ce443c42a2bacf2645bfe7e603
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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