Potassium Carbonate → HCID 68815400, compound

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[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:39][C:40]([O:42][CH3:43])=[O:41]>CC(C)=O>[CH3:43][O:42][C:40](=[O:41])[CH2:39][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]([CH3:31])=[C:10]3[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:18][CH:19]=1

Participants

Procedure

The desired product was prepared using a procedure similar to step 1 of example 4. Thus, 4-(1,3-dibenzyl-2-methyl-1H-indol-5-yl)-phenol (0.155 g, 0.384 mmol) was reacted with K2CO3 (0.069 g, 0.499 mmol) and methyl bromoacetate (0.076 g, 0.499 mmol) in acetone (5 ml) to give the product (0.152 g, 0.320 mmol, 83%) as a viscous oil. 1H NMR (DMSO-d6) δ 2.35 (s, 3H), 3.70 (s, 3H), 4.10 (s, 2H), 4.80 (s, 2H), 5.42 (s, 2H), 6.94-7.00 (m, 4H), 7.09-7.13 (m, 1H), 7.20-7.30 (m, 8H), 7.39 (d, J=8.6 Hz, 1H), 7.49 (d, J=8.9 Hz, 2H), 7.58 (d, J=1.7 Hz, 1H); [ESI(+)], m/z 476 (M+H)+.