Potassium Carbonate → HCID 68814065, compound

HRID 731038Notes

Reaction equation

HRID 731038 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]([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: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]([CH3:25])=[C:10]3[CH3:24])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68814853HCID 68814853, compound

Product 1

HCID 68814065HCID 68814065, 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-2,3-dimethyl-1H-indol-5-yl)-phenol (0.300 g, 0.916 mmol) was reacted with K2CO3 (0.152 g, 1.099 mmol) and methyl bromoacetate (0.168 g, 1.099 mmol) in acetone (10 ml) to give the product (0.233 g, 0.583 mmol, 64%) as a purple solid, mp 133-136° C. 1H NMR (DMSO-d6) δ 2.24 (s, 3H), 2.28 (s, 3H), 3.71 (s, 3H), 4.82 (s, 2H), 5.39 (s, 2H), 6.98 (d, J=8.6 Hz, 4H), 7.20 (t, J=7.2 Hz, 1H), 7.26-7.29 (m, 3H), 7.37 (d, J=8.4 Hz, 1H), 7.58 (d, J=8.7 Hz, 2H), 7.62 (s, 1H); [ESI(+)], m/z 400 (M+H)+.

Sources & evidence

ORD record
ord-3f9cdbfe4f50469389d24ce96227b229
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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