Potassium Carbonate → HCID 68814430, compound

HRID 731050Notes

Reaction equation

HRID 731050 reaction equation
[CH3:1][N:2]1[C:14]2[CH:13]=[CH:12][C:11]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[CH:10][C:9]=2[C:8]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=2.C([O-])([O-])=O.[K+].[K+].Br[CH2:29][C:30]#[N:31]>CC(C)=O>[CH3:1][N:2]1[C:14]2[CH:13]=[CH:12][C:11]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:29][C:30]#[N:31])=[CH:19][CH:20]=3)=[CH:10][C:9]=2[C:8]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68815892HCID 68815892, compound

Product 1

HCID 68814430HCID 68814430, 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-(9-methyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenol (0.194 g, 0.699 mmol) was reacted with K2CO3 (0.116 g, 0.839 mmol) and bromoacetonitrile (0.101 g, 0.839 mmol) in acetone (8 ml) to give the product (0.153 g, 0.484 mmol, 69%) as a white solid, mp 204-206° C. 1H NMR (DMSO-d6) δ 1.77-1.82 (m, 2H), 1.84-1.90 (m, 2H), 2.67 (t, J=5.8 Hz, 2H), 2.72 (t, J=5.8 Hz, 2H), 3.61 (s, 3H), 5.19 (s, 2H), 7.12 (d, J=8.7 Hz, 2H), 7.33 (dd, J=1.4, 8.4 Hz, 1H), 7.40 (d, J=8.6 Hz, 1H), 7.59 (s, 1H), 7.65 (d, J=8.6 Hz, 2H); [ESI(+)], m/z 317 (M+H)+.

Sources & evidence

ORD record
ord-d79d2e1ed8a04288a3e4d067bd3d5eed
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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