Triphenylphosphine → HCID 67314508, compound

HRID 1012676Notes

Reaction equation

HRID 1012676 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[CH:22]=[C:21](Br)[CH:20]=[CH:19][C:18]=2[CH3:24])=[O:16])=[C:11]([Cl:25])[CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:45]([Si:47]([CH3:50])([CH3:49])[CH3:48])#[CH:46]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[CH:22]=[C:21]([C:46]#[C:45][Si:47]([CH3:50])([CH3:49])[CH3:48])[CH:20]=[CH:19][C:18]=2[CH3:24])=[O:16])=[C:11]([Cl:25])[CH:10]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 67314056HCID 67314056, compound

Product 1

HCID 67314508HCID 67314508, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
90 °C

Procedure

In a screw-capped vial (8 mL) was placed dry degassed triethylamine (3.0 mL) and a magnetic stirrer under argon. Compound 543 (200 mg, 0.48 mmol), Pd2(dba)3 (9.0 mg, 0.01 mmol), triphenyl phosphine (13 mg, 0.048 mmol), CuI (2 mg) and ethynyl-trimethyl-silane (66 μL, 0.48 mmol) were added to the vial and the reaction mixture was heated under vigorously stirring at 90° C. for 20 h. The cooled reaction mixture was filtered through Decalite and concentrated in vacuo. The crude product was purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) (v:v=5:95 to 30:70) as the eluent to afford the title compound as yellow foam.

Workup

  1. customIn a screw-capped vial (8 mL) was placed dry
  2. customdegassed triethylamine (3.0 mL) and a magnetic stirrer under argon
  3. temperaturewas heated
  4. customThe cooled reaction mixture
  5. filtrationwas filtered through Decalite
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-c7b3cf75c617480cb7d88e995c7cbe86
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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