Triphenylphosphine → HCID 67131823, compound

HRID 906930Notes

Reaction equation

HRID 906930 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH:10]([CH:21]([O:23][C:24]2[CH:29]=[CH:28][C:27](Br)=[CH:26][N:25]=2)[CH3:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:50]([Si:52]([CH3:55])([CH3:54])[CH3:53])#[CH:51]>C1COCC1.C(NCC)C.C(OCC)(=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH:10]([CH:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C:51]#[C:50][Si:52]([CH3:55])([CH3:54])[CH3:53])=[CH:26][N:25]=2)[CH3:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 67131595HCID 67131595, compound

Product 1

HCID 67131823HCID 67131823, compoundYield 68%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8021DiethylamineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 2-{(SR)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-5-bromo-pyridine (128 mg, 0.253 mmol) and bis(triphenylphosphine) palladium(II) chloride (53 mg, 0.076 mmol) and triphenylphosphine (16.6 mg, 0.0632 mmol) and CuI (11 mg, 0.0578 mmol) in THF (3 mL) and diethylamine (1.5 mL) was added ethynyltrimethylsilane (0.108 mL, 0.759 mmol) under Ar. The mixture was heated at 85° C. over night. The reaction mixture was diluted with ethyl acetate and washed with aq.ammonium chloride solution two times. The separated organic phase was dried over anhydrous sodium sulfate and concentrated in vaccuo after filtration. The residue was purified by silica gel column chromatography (DCM) yielding 89.5 mg (68%) of the titled compound as a light yellow oil. ES-MS m/e: 523.3 (M+H+).

Workup

  1. washwashed with aq
  2. dry with materialThe separated organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vaccuo
  4. filtrationafter filtration
  5. customThe residue was purified by silica gel column chromatography (DCM)

Sources & evidence

ORD record
ord-1e58f6c5f08f497392fec00311cb0c59
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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