Benzenepropanoyl chloride → HCID 71224410, compound

HRID 2402946Notes

Reaction equation

HRID 2402946 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([Sn](C)(C)C)[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:5][N:4]=1.[C:18]1([CH2:24][CH2:25][C:26](Cl)=[O:27])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.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.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.[Pd]>[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:26](=[O:27])[CH2:25][CH2:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 64801Benzenepropanoyl chlorideHCID 71223985HCID 71223985, compound

Product 1

HCID 71224410HCID 71224410, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of Example 6A (600 mg, 1.74 mmol) in toluene (20 ml) was added palladium tetrakis(triphenylphosphine) (96 mg, 0.08 mmol) and 3-phenylpropanoyl chloride (0.37 ml, 2.5 mmol). The reaction mixture was purged with nitrogen and heated at 100° C. for 12 hours. After cooling, the reaction mixture was directly separated by flash chromatography which was eluted with 15% ethyl acetate in hexane to provide the title compound. MS (DCI/NH3) m/z 303 (M+H)+.

Workup

  1. customThe reaction mixture was purged with nitrogen
  2. temperatureAfter cooling
  3. customthe reaction mixture was directly separated by flash chromatography which
  4. washwas eluted with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-bd6e330814ea47349f24835f0b694eb4
Source dataset
uspto-grants-2014_08
Patent number
US08796289B2

Reaction notes

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