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Piperidine → Tert-butyl[(1-{[3-(propylsulfonyl)phenyl]ethynyl}-2-naphthyl)oxy]acetate

HRID 2390273
Notes
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Reaction equation

HRID 2390273 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1Br)([CH3:4])([CH3:3])[CH3:2].[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH2:32][CH2:33][CH3:34])(=[O:31])=[O:30])[CH:24]=1)#[CH:22].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1CCCCC1>O.CC(C)=O.[Pd](Cl)Cl>[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[C:22]#[C:21][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH2:32][CH2:33][CH3:34])(=[O:31])=[O:30])[CH:24]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8082PiperidineHCID 11776TriphenylphosphineHCID 565942671-Ethynyl-3-(propylsulfonyl)benzeneHCID 58522023tert-Butyl[(1-bromo-2-naphthyl)oxy]acetate2×

Product 1

HCID 58521954Tert-butyl[(1-{[3-(propylsulfonyl)phenyl]ethynyl}-2-naphthyl)oxy]acetate

Reagents, catalysts & solvents 3

HCID 24290
Palladium Chloride
Catalyst
HCID 180AcetoneSolvent
HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (1-bromo-naphthalen-2-yloxy)-acetic acid tert-butyl ester (Intermediate 217; 500 mg; 1.48 mmol), 1-ethynyl-3-(propane-1-sulfonyl)-benzene (618 mg; 2.97 mmol) and PPh3 (39 mg; 0.15 mmol) in water (4.40 ml) and Acetone (5.6 ml) was treated with palladium(II) chloride (13 mg; 0.07 mmol) and piperidine (295 μl; 2.97 mmol) and heated at 60° C. for 2 days. The reaction mixture was extracted with EtOAc, the organic phase was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the title compound as a yellow sticky solid.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. dry with materialthe organic phase was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by flash column chromatography (silica)
  5. washeluting with cyclohexane containing
  6. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-901b093ed95c443f82efc5ecf792a660
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08273769B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes