Water → HCID 90417345, compound

HRID 588271Notes

Reaction equation

HRID 588271 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C(N(CC)CC)C.[CH2:19]([O:21][CH:22]([O:25][CH2:26][CH3:27])[C:23]#[CH:24])[CH3:20].O>C1COCC1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[CH2:19]([O:21][CH:22]([O:25][CH2:26][CH3:27])[C:23]#[C:24][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2)[CH3:20]

Participants

9

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 662853,3-DiethoxypropyneHCID 98380455-Iodoindolin-2-one

Product 1

HCID 90417345HCID 90417345, compoundYield 59.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-iodo-2-oxoindoline (497 mg, 1.9 mmol) in THF (20 ml) were added triethylamine (0.80 ml, 5.7 mmol), 3,3-diethoxyprop-1-yne (738 mg, 5.7 mmol), CuI (73 mg, 0.38 mmol) and Pd(PPh3)4 (222 mg, 0.19 mmol). The reaction mixture was stirred for 4 h at 50° C. The mixture was poured into H2O and EtOAc. The mixture was separated into an aqueous layer and an organic layer. The aqueous layer was extracted with ethyl acetate 3 times. The combined organic layer was washed with sat. NaHCO3 solution, and brine, and then dried over Na2SO4. The solvent was evaporated and the residue purified by column chromatography (EtOAc then CHCl3/MeOH) to give 5-(3,3-diethoxyprop-1-ynyl)indolin-2-one as a brown solid (292 mg, 59%).

Workup

  1. customThe mixture was separated into an aqueous layer
  2. extractionThe aqueous layer was extracted with ethyl acetate 3 times
  3. washThe combined organic layer was washed with sat. NaHCO3 solution, and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated
  6. customthe residue purified by column chromatography (EtOAc

Sources & evidence

ORD record
ord-db029b86dbf6450b8da71cdcfd9c91d8
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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