Water → tert-butyl (E)-4-[2-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)vinyl]piperidine-1-carboxylate

HRID 1749998Notes

Reaction equation

HRID 1749998 reaction equation
CC1(C)C(C)(C)OB(/[CH:9]=[CH:10]/[CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)O1.I[C:26]1[C:34]2[O:33][CH2:32][C:31](=[O:35])[C:30]=2[CH:29]=[CH:28][C:27]=1[O:36][CH3:37].C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.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>[CH3:37][O:36][C:27]1[CH:28]=[CH:29][C:30]2[C:31](=[O:35])[CH2:32][O:33][C:34]=2[C:26]=1/[CH:9]=[CH:10]/[CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:15][CH2:16]1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 68447302(e)-Tert-butyl 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)piperidine-1-carboxylateHCID 712788737-iodo-6-methoxybenzofuran-3(2H)-one

Product 1

HCID 86682082tert-butyl (E)-4-[2-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)vinyl]piperidine-1-carboxylateYield 27.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (E)-4-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl]piperidine-1-carboxylate (0.253 g, 0.750 mmol) in 1,4-dioxane (5 mL) was added with 7-iodo-6-methoxybenzofuran-3(2H)-one (0.198 g, 0.682 mmol) synthesized in Example B46, Step 2, 2 M aqueous sodium carbonate (0.680 mL, 1.36 mmol) and tetrakis(triphenylphosphine)palladium (0.0788 g, 0.0682 mmol), and the mixture was refluxed for 10 hours by heating. The reaction mixture was cooled to room temperature, and then added with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was subjected to silica gel column chromatography (chloroform/methanol), and the resulting crude product was further purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl (E)-4-[2-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)vinyl]piperidine-1-carboxylate (0.0692 g, 27%).

Workup

  1. temperaturethe mixture was refluxed for 10 hours
  2. temperatureby heating
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customthe resulting crude product was further purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1df6111f85934d8684ef73e72df93684
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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