Triphenylphosphine → HCID 86583540, compound

HRID 1016768Notes

Reaction equation

HRID 1016768 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:10]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:44][Si:45]([C:48]#[CH:49])([CH3:47])[CH3:46]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([NH:16][CH:10]([C:4]2[CH:3]=[C:2]([C:49]#[C:48][Si:45]([CH3:47])([CH3:46])[CH3:44])[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:18][CH:19]=1)#[N:24]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 86583541HCID 86583541, compound

Product 1

HCID 86583540HCID 86583540, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

403 mg of the ethyl (RS)-(3-bromo-5-hydroxymethyl-phenyl)-(4-cyano-phenylamino)-acetate described in Example 156.2 were suspended in 3.1 ml of triethylamine and 4 mg of triphenylphosphine were added. Argon was conducted through the reaction mixture for 30 min. Then, 7 mg of palladium(II) acetate and 0.22 ml of trimethylsilylacetylene were added and the mixture was heated for 26 hrs. to 80° C. Then, the mixture was left to cool to room temperature and the crude product was isolated by extraction and purified by column chromatography (n-hexane/ethyl acetate). There were obtained 398 mg of ethyl (RS)-(4-cyano-phenylamino)-(3-hydroxymethyl-5-trimethylsilanylethynyl-phenyl)-acetate as a brown oil; MS: 406 ([M]+).

Workup

  1. temperaturethe mixture was heated for 26 hrs
  2. customto 80° C
  3. waitThen, the mixture was left
  4. customthe crude product was isolated by extraction
  5. custompurified by column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f4786ad761834479bad967780eab87e3
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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