Potassium Carbonate → HCID 68815874, compound

HRID 731098Notes

Reaction equation

HRID 731098 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]#[N:38]>CC(C)=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:36][C:37]#[N:38])=[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:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68814272HCID 68814272, compound

Product 1

HCID 68815874HCID 68815874, 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-methyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenol (0.173 g, 0.472 mmol) was reacted with K2CO3 (0.078 g, 0.566 mmol) and bromoacetonitrile (0.068 g, 0.566 mmol) in acetone (10 ml) to give the product (0.160 g, 0.392 mmol, 83%) as a white solid, mp 101-102° C. 1H NMR (DMSO-d6) δ 0.76 (t, J=7.0 Hz, 3H), 1.14-1.22 (m, 4H), 1.52-1.98 (m, 2H), 2.66 (t, J=7.5 Hz, 2H), 3.56 (s, 3H), 5.21 (s, 2H), 7.16 (d, J=8.9 Hz, 2H), 7.43-7.51 (m, 5H), 7.55 (t, J=7.2 Hz, 2H), 7.69 (d, J=8.9 Hz, 2H), 7.76 (d, J=1.1 Hz, 1H); [ESI(+)], m/z 409 (M+H)+.

Sources & evidence

ORD record
ord-eda2776bd09d456eaba74ec4ef71b232
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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