Triphenylphosphine → HCID 178497560, compound

HRID 46142Notes

Reaction equation

HRID 46142 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:24])[S:12][C:11]([NH:13][C@H:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH3:15])=[N:10][C:9]2=[O:23])=[CH:4][CH:3]=1.[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:44]([O-:47])(=[O:46])C.[K+].[C]=O>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C@@H:14]([NH:13][C:11]2[S:12][C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:44]([O:47][CH3:25])=[O:46])=[CH:3][CH:4]=3)([CH3:24])[C:9](=[O:23])[N:10]=2)[CH3:15])=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 178418416HCID 178418416, compoundHCID 178461983HCID 178461983, compound

Product 1

HCID 178497560HCID 178497560, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(4-bromophenyl)-2-((S)-1-(4fluorophenyl)ethylamino)-5-methylthiazol-4(5H)-one (0.79 g, 1.9 mmol), triphenylphosphine (Aldrich, 0.15 g, 0.58 mmol), palladium acetate (Aldrich, 0.11 g, 0.48 mmol), potassium acetate (Aldrich, 0.24 g, 2.4 mmol), in MeOH (3 mL) and DMF (3 mL) was pressurized with carbon monoxide, purged twice with CO and then heated to 100° C. overnight at 40-50 psi of CO. After the reaction mixture was cooled to ambient temp., then contents were filtered through Celite. The Celite pad was washed with CH2Cl2, and the organic phase was dried over Na2SO4, concentrated in vacuo. The crude material was purified using silica gel chromatography. MS: 387 (M+1).

Workup

  1. custompurged twice with CO
  2. temperatureAfter the reaction mixture was cooled to ambient temp.
  3. filtrationcontents were filtered through Celite
  4. washThe Celite pad was washed with CH2Cl2
  5. dry with materialthe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified

Sources & evidence

ORD record
ord-4c3dad1ce45246e898598a0511c17bcb
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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