Triphenylphosphine → HCID 68686090, compound

HRID 2238653Notes

Reaction equation

HRID 2238653 reaction equation
[C:1]([O:3][CH2:4][CH3:5])#[CH:2].B.O1CCCC1.I[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])[CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3]/[CH:4]=[CH:5]/[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])[CH:14]=1)[CH3:2]

Participants

9

Reactant 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 61239Ether, ethyl ethynylHCID 2723981Borane;tetrahydrofuranHCID 68688975HCID 68688975, compound

Product 1

HCID 68686090HCID 68686090, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.3 mL of ethyl ethynyl ether (50% v/v hexane solution) was dissolved in 10 mL of tetrahydrofuran, and in an ice bath, 2.04 mL of borane-tetrahydrofuran complex (1.0M tetrahydrofuran solution) was added dropwise over 30 minutes. Thereafter, the reaction mixture was heated to room temperature, and stirred for 3 hours. Thereto, 10 mL of tetrahydrofuran solution containing 330 mg of the 4-iodo-N-[(1S)-1-phenylethyl]-2-pyridinamine [58-1], 11.5 mg of palladium acetate, 40.2 mg of triphenylphosphine, and 1.28 mL of a 4N aqueous solution of sodium hydroxide, were added, and further stirred at room temperature for 5 hours. The reaction mixture was diluted with 150 mL of ethyl acetate, washed with water and saturated brine in the subsequent order, and the thus obtained organic layer was dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, to obtain 94 mg of 4-[(E)-2-ethoxyethenyl]-N-[(1S)-1-phenylethyl]-2-pyridinamine [58-2] as a brown oily product.

Workup

  1. additionwere added
  2. stirringfurther stirred at room temperature for 5 hours
  3. washwashed with water and saturated brine in the subsequent order
  4. dry with materialthe thus obtained organic layer was dried over anhydrous magnesium sulfate
  5. filtrationThe insolubles were filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-143f11f7d94c44c48d0794b4494d7d1a
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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