Triphenylphosphine → HCID 86713168, compound

HRID 1500279Notes

Reaction equation

HRID 1500279 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9]O)=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrN1C(=O)CCC1=O.[CH3:38][S:39]([O-:41])=[O:40].[Na+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][S:39]([CH3:38])(=[O:41])=[O:40])=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 2733271Sodium methanesulfinateHCID 534036882-(5-Bromopyridin-2-yl)ethan-1-ol

Product 1

HCID 86713168HCID 86713168, compoundYield 46.4%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

The product of Step 1 of Example 6 (940 mg, 4.65 mmol) in dimethylformamide (5 mL) at 5° C. is treated with triphenylphosphine (1710 mg, 6.5 mmol) and N-bromosuccinimide (1.24 g, 7.0 mmol) then stirred for 1 hour. Sodium methanesulfinate (980 mg, 9.3 mmol) and tetrabutylammonium iodide (175 mg, 0.45 mmol) are added and the mixture heated at 70° C. for 1 hour then cooled to room temperature, diluted with ethyl acetate (25 mL), washed with water (25 mL) and brine (25 mL), dried over MgSO4, filtered, concentrated, and the crude material purified by column chromatography on silica gel eluting with a gradient of ethyl acetate/heptane to afford the title compound (570 mg): m/z (Cl) 265 [M+H].

Workup

  1. temperaturethen cooled to room temperature
  2. washwashed with water (25 mL) and brine (25 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe crude material purified by column chromatography on silica gel eluting with a gradient of ethyl acetate/heptane

Sources & evidence

ORD record
ord-a56d1c538f34431897332f8131d2d560
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

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