Potassium Carbonate → [4-(1-Benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetic acid methyl ester

HRID 731093Notes

Reaction equation

HRID 731093 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][CH2:25][CH2:26][CH2:27][CH3:28])=[C:9]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:42][C:43]([O:45][CH3:46])=[O:44]>CC(C)=O>[CH3:46][O:45][C:43](=[O:44])[CH2:42][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:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[C:10]3[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 688155514-(1-Benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenol

Product 1

HCID 68814967[4-(1-Benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetic acid methyl ester

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-pentyl-2-phenyl-1H-indol-5-yl)-phenol (0.300 g, 0.673 mmol) was reacted with K2CO3 (0.121 g, 0.875 mmol) and methyl bromoacetate (0.134 g, 0.875 mmol) in acetone (10 ml) to give the product (0.296 g, 0.572 mmol, 85%) as a white, waxy solid, mp 106-109° C. 1H NMR (DMSO-d6) δ 0.72 (t, J=7.0 Hz, 3H), 1.09-1.19 (m, 4H), 1.49-1.56 (m, 2H), 2.64 (t, J=7.5 Hz, 2H), 3.68 (s, 3H), 4.79 (s, 2H), 5.23 (s, 2H), 6.79-6.81 (m, 2H), 6.97 (d, J=8.9 Hz, 2H), 7.09-7.18 (m, 3H), 7.29-7.34 (m, 4H), 7.37-7.47 (m, 3H), 7.55 (d, J=8.9 Hz, 2H), 7.72 (d, J=0.7 Hz, 1H); [ESI(+)], m/z 519 (M+H)+.

Sources & evidence

ORD record
ord-27b6544119244532b8b0644c1d46350c
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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