Ozone → HCID 68814795, compound

HRID 731079Notes

Reaction equation

HRID 731079 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH:13]=[CH:14][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.O=[O+][O-].Br[CH2:35][C:36]([O:38][CH3:39])=[O:37]>CC(C)=O>[CH3:39][O:38][C:36](=[O:37])[CH2:35][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[C:10]([CH3:24])=[C:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N: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 24823OzoneHCID 60984Methyl bromoacetateHCID 68815056HCID 68815056, compound

Product 1

HCID 68814795HCID 68814795, 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-benzyl-3-methyl-2-phenyl-1H-indol-4-yl)-phenol (0.260 g, 0.668 mmol) was reacted with K2C(O3 (0.120 g, 0.868 mmol) and methyl bromoacetate (0.133 g, 0.868 mmol) in acetone (5 ml) to give the product (0.271 g, 0.587 mmol, 88%) as a viscous oil. 1H NMR (DMSO-d6) δ 1.72 (s, 3H), 3.71 (s, 3H), 4.84 (s, 2H), 5.29 (s, 2H), 6.84 (d, J=7.0 Hz, 1H), 6.88 (d, J=7.2 Hz, 2H), 6.98 (d, J=8.7 Hz, 2H), 7.11 (t, J=7.3 Hz, 1H), 7.16 (t, J=7.2 Hz, 1H), 7.22 (t, J=7.0 Hz, 2H), 7.31-7.35 (m, 5H), 7.41 (t, J=7.2 Hz, 1H), 7.45 (t, J=7.5 Hz, 2H); [ESI(+)], m/z 462 (M+H)+.

Sources & evidence

ORD record
ord-1f12565e1b15491e895c0666c0ed5f1a
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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