Potassium Iodide → HCID 18522128, compound

HRID 413801Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:14][N:15]1[C:23]2[C:18](=[C:19]([O:24][CH2:25][CH2:26]Br)[CH:20]=[CH:21][CH:22]=2)[CH:17]=[C:16]1[C:28]([O:30][CH3:31])=[O:29].[I-].[K+]>C(#N)C>[Cl:10][C:11]1[CH:12]=[C:13]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:14][N:15]1[C:23]2[C:18](=[C:19]([O:24][CH2:25][CH2:26][N:7]3[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]3)[CH:20]=[CH:21][CH:22]=2)[CH:17]=[C:16]1[C:28]([O:30][CH3:31])=[O:29]

Participants

Conditions

Temperature: 80 °C

Procedure

1-(2-Hydroxyethyl)piperazine (175 mg) was added to a stirred solution of methyl N-(3,4-dichlorobenzyl)-4-(bromoethyloxy)indole-2-carboxylate (278 mg) and potassium iodide (10 mg) in acetonitrile (15 ml). The reaction was heated at 80° C. for 16 hours. The reaction was concentrated in vacuo and the residue dissolved in ethyl acetate, washed with water, saturated aqueous sodium chloride solution and dried (MgSO4). The solvent was removed in vacuo to give the product as a colourless oil (215 mg, 70%); NMR d (CD3SOCD3) 2.31-2.57 (m, 10H), 2.78 (t, 2H), 3.47 (dd, 2H), 3.80 (s, 3H), 4.20 (t, 2H), 4.30 (t, 1H), 5.79 (s, 2H), 6.61 (d, 1H), 6.88 (dd, 1H), 7.13 (d, 1H), 7.22 (t, 1H), 7.29-7.32 (m, 2H), 7.51 (d, 1H); M/z (+) 506 (MH+).

Workup

concentrationThe reaction was concentrated in vacuo
dissolutionthe residue dissolved in ethyl acetate
washwashed with water, saturated aqueous sodium chloride solution
dry with materialdried (MgSO4)
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-47622db8429147c3890a34bfc33ce9e3
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06569888B1

Reaction notes

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