Toluene → 1-(2-Diethylaminoethyl)-4-bromo-6-[3-(2-oxo-1-imidazolidinyl)-1-propynyl]-3-hydroxy-3-(2-chlorophenyl)oxindole

HRID 1369100Notes

Reaction equation

HRID 1369100 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([Br:16])[CH:11]=[C:12](I)[CH:13]=2)[C:8]([OH:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:7]1=[O:25])[CH3:2].[O:28]=[C:29]1[NH:33][CH2:32][CH2:31][N:30]1[CH2:34][C:35]#[CH:36].CCN(CC)CC.C1(C)C=CC=CC=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C1COCC1>[CH2:1]([N:3]([CH2:26][CH3:27])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([Br:16])[CH:11]=[C:12]([C:36]#[C:35][CH2:34][N:30]3[CH2:31][CH2:32][NH:33][C:29]3=[O:28])[CH:13]=2)[C:8]([OH:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:7]1=[O:25])[CH3:2]

Participants

8

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 156696571-(Prop-2-yn-1-yl)imidazolidin-2-oneHCID 185186541-(2-Diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-bromo-6-iodooxindole

Product 1

HCID 185185471-(2-Diethylaminoethyl)-4-bromo-6-[3-(2-oxo-1-imidazolidinyl)-1-propynyl]-3-hydroxy-3-(2-chlorophenyl)oxindoleYield 92%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 1-(2-diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-bromo-6-iodooxindole (25.0 mg, 4.64×10−5 mol), 3-(2-oxo-1-imidazolidinyl)-1-propyne (8.6 mg, 1.5 eq.), Pd(PPh3)2Cl2 (4.88 mg, 15 mol %) and CuI (1.32 mg, 15 mol %) under a nitrogen atmosphere was added anhydrous Et3N (0.5 mL), anhydrous toluene (0.5 mL) and anhydrous THF (0.5 mL). The resulting yellow mixture was heated to 50° C. (bath temperature) and stirred at that temperature for 1 hour 20 minutes. The solvent was then removed in vacuo to give a yellow solid. Purification was carried out by column chromatography (silica gel, 6% MeOH in CHCl3) to yield the title compound (23.9 mg, 92%) as a light brown solid.

Workup

  1. customThe solvent was then removed in vacuo
  2. customto give a yellow solid
  3. customPurification

Sources & evidence

ORD record
ord-b119519dc6ab49108fdd72e2a428f7b6
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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