Potassium Carbonate → HCID 68814203, compound

HRID 731036Notes

Reaction equation

HRID 731036 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]#[N:35]>CC(C)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH2:33][C:34]#[N:35])=[CH:21][CH:22]=3)=[CH:14][CH:15]=2)[C:10]([CH3:24])=[C:9]1[CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68814853HCID 68814853, compound

Product 1

HCID 68814203HCID 68814203, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The desired product was prepared using a procedure similar to step 5 of example 3. 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 bromoacetonitrile (0.132 g, 1.099 mmol) in acetone (10 ml) to give the product (0.207 g, 0.565 mmol, 62%) as a pale-blue solid, mp 167-169° C. 1H NMR (DMSO-d6) δ 2.25 (s, 3H), 2.28 (s, 3H), 5.19 (s, 2H), 5.39 (s, 2H), 6.98 (d, J=7.5 Hz, 2H), 7.12 (d, J=8.6 Hz, 2H), 7.21 (t, J=7.2 Hz, 1H), 7.26-7.30 (m, 3H), 7.39 (d, J=8.4 Hz, 1H), 7.65-7.67 (m, 3H); [ESI(+)], m/z 367 (M+H)+.

Sources & evidence

ORD record
ord-1b6f33bbd8244376ae150588d4d4c539
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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