Potassium Carbonate → HCID 68814951, compound

HRID 731072Notes

Reaction equation

HRID 731072 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[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.C([O-])([O-])=O.[K+].[K+].Br[CH2:38][C:39]([O:41][CH3:42])=[O:40]>CC(C)=O>[CH3:42][O:41][C:39](=[O:40])[CH2:38][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]2[CH:15]=[C:16]3[C:11]([C:10]([CH3:24])=[C:9]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:8]3[CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:12][CH:13]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68814691HCID 68814691, compound

Product 1

HCID 68814951HCID 68814951, 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-6-yl)-phenol (0.291 g, 0.747 mmol) was reacted with K2CO3 (0.134 g, 0.971 mmol) and methyl bromoacetate (0.149 g, 0.971 mmol) in acetone (5 ml) to give the product (0.305 g, 0.661 mmol, 88%) as a white solid, mp 145-148° C. 1H NMR (DMSO-d6) δ 2.24 (s, 3H), 3.70 (s, 3H), 4.81 (s, 2H), 5.39 (s, 2H), 6.86 (d, J=7.2 Hz, 2H), 6.98 (d, J=8.9 Hz, 2H), 7.13 (t, J=7.2 Hz, 1H), 7.18 (t, J=7.0 Hz, 2H), 7.34 (dd, J=1.4, 8.1 Hz, 1H), 7.39-7.44 (m, 3H), 7.49 (t, J=7.0 Hz, 2H,) 7.56-7.62 (m, 4H); [ESI(+)], m/z 462 (M+H)+.

Sources & evidence

ORD record
ord-959468c9546f4d5ebe84d89dc251e486
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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