Potassium Carbonate → HCID 68814817, compound

HRID 731065Notes

Reaction equation

HRID 731065 reaction equation
[CH2:1]([C: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)[N:10]([CH3:24])[C:9]=1[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:33][C:34]([O:36][CH3:37])=[O:35]>CC(C)=O>[CH3:37][O:36][C:34](=[O:35])[CH2:33][O:23][C:20]1[CH:19]=[CH:18][C:17]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[N:10]([CH3:24])[C:9]([CH3:25])=[C:8]3[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68814801HCID 68814801, compound

Product 1

HCID 68814817HCID 68814817, 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-(3-benzyl-1,2-dimethyl-1H-indol-5-yl)-phenol (0.162 g, 0.495 mmol) was reacted with K2CO3 (0.089 g, 0.643 mmol) and methyl bromoacetate (0.098 g, 0.643 mmol) in acetone (5 ml) to give the product (0.161 g, 0.403 mmol, 81%) as an off-white solid, mp 113-117° C. 1H NMR (DMSO-d6) δ 2.40 (s, 3H), 3.67 (s, 3H), 3.70 (s, 3H), 4.06 (s, 2H), 4.80 (s, 2H), 6.96 (d, J=8.9 Hz, 2H), 7.08-7.11 (m, 1H), 7.19-7.24 (m, 4H), 7.29 (dd, J=1.7, 8.4 Hz, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.51 (d, J=8.9 Hz, 2H), 7.56 (d, J=1.5 Hz, 1H); [ESI(+)], m/z 400 (M+H)+.

Sources & evidence

ORD record
ord-421ebed02f464b2bb556f9046edd52c5
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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