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

HRID 1369099Notes

Reaction equation

HRID 1369099 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].C([NH:30][C:31]([NH:33][CH2:34][C:35]#[CH:36])=[O:32])C.[CH3:37][CH2:38]N(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:33]([CH2:37][CH3:38])[C:31]([NH2:30])=[O:32])[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 14344953N-ethyl-N'-propargylureaHCID 185186541-(2-Diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-bromo-6-iodooxindole

Product 1

HCID 185185791-(2-Diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-bromo-6-[3-(N-ethylureido)-1-propynyl]oxindoleYield 86%

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 (21.0 mg, 3.89×10−5 mol), N-ethyl-N′-propargylurea (7.36 mg, 1.5 eq.), Pd(PPh3)2Cl2 (4.10 mg, 15 mol %) and CuI (1.10 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 2 hours. The solvent was then removed in vacuo to give a yellow solid. Purification was carried out by column chromatography (silica gel, 10% MeOH in CHCl3) to yield the title compound (18.8 mg, 86%) 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-790bb2b6ffcc4052b2e0c9e34e977a5a
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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