Potassium Carbonate → HCID 68814276, compound

HRID 731100Notes

Reaction equation

HRID 731100 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[C:4]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:3]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:36][C:37]([O:39][CH3:40])=[O:38]>CC(C)=O>[CH3:40][O:39][C:37](=[O:38])[CH2:36][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:2]([CH3:1])[C:3]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:4]3[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68814272HCID 68814272, compound

Product 1

HCID 68814276HCID 68814276, 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-methyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenol (0.180 g, 0.491 mmol) was reacted with K2CO3 (0.088 g, 0.639 mmol) and methyl bromoacetate (0.098 g, 0.639 mmol) in acetone (5 ml) to give the product (0.184 g, 0.417 mmol, 85%) as a viscous oil. 1H NMR (DMSO-d6) δ 0.76 (t, J=7.2 Hz, 3H), 1.15-1.22 (m, 4H), 1.51-1.56 (m, 2H), 2.65 (t, J=7.3 Hz, 2H), 3.56 (s, 3H), 3.71 (s, 3H), 4.83 (s, 2H), 7.01 (d, J=8.6 Hz, 2H), 7.41-7.45 (m, 3H), 7.47-7.50 (m, 2H), 7.54 (t, J=7.2 Hz, 2H), 7.61 (d, J=8.6 Hz, 2H), 7.73 (s, 1H); [ESI(+)], m/z 442 (M+H)+.

Sources & evidence

ORD record
ord-65027de6cba64fffa6af2e57eb8c51bd
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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