Ammonium Chloride → HCID 18452898, compound

HRID 1271516Notes

Reaction equation

HRID 1271516 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](OS(C(F)(F)F)(=O)=O)=[CH:5][C:4]=1[F:17])#[N:2].[Br-].[CH2:19]([Zn+])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1.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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:19]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:17])[CH:5]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 10880116HCID 10880116, compoundHCID 178419772HCID 178419772, compound

Product 1

HCID 18452898HCID 18452898, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

To a room temperature solution of 1.5 g (5.57 mmol) of the triflate from Step A above, 0.32 g (0.56 mmol) of bis(dibenzylideneacetone)palladium and 1,1′-bis(diphenylphosphino)-ferrocene in 15 mL of tetrahydrofuran is added to 12.25 mL (6.13 mmol) of a 0.5 M solution of benzylzinc bromide in tetrahydrofuran via syringe. The mixture is heated to 65° C. for 16 hr and cooled to room temperature. The mixture is poured into saturated ammonium chloride and extracted two times with ethyl acetate. The combined organic portions are dried (MgSO4), filtered, and concentrated in vacuo. Chromatography (Biotage, 100% toluene) of the residue affords 0.76 g (65%) of the title compound.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted two times with ethyl acetate
  3. dry with materialThe combined organic portions are dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-424063a39c10426b91104d7f9687f26e
Source dataset
uspto-grants-2007_04
Patent number
US07205313B2

Reaction notes

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