Potassium Carbonate → HCID 68815400, compound

HRID 731058Notes

Reaction equation

HRID 731058 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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68814952HCID 68814952, compound

Product 1

HCID 68815400HCID 68815400, 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-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)+.

Sources & evidence

ORD record
ord-ad0d4146c5624004bd9db15002ccf091
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

Loading…