Benzylamine → HCID 58136544, compound

HRID 877166Notes

Reaction equation

HRID 877166 reaction equation
[CH3:1][C:2]1([C:19]([O:21][CH3:22])=[O:20])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2OS(C(F)(F)F)(=O)=O)[CH2:3]1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>O1CCOCC1.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]>[CH2:23]([NH:30][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH2:10][C:2]([CH3:1])([C:19]([O:21][CH3:22])=[O:20])[CH2:3]2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 58136322HCID 58136322, compound

Product 1

HCID 58136544HCID 58136544, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Under argon, a solution of 1 g (2.96 mmol) of methyl 2-methyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1H-indene-2-carboxylate, 290 μl (2.66 mmol) of benzylamine, 2.41 g (7.29 mmol) of cesium carbonate, 56 mg (0.12 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl and 54 mg (0.059 mmol) of tris(dibenzylideneaceton)dipalladium in 50 ml of dioxane was stirred at a bath temperature of 100° C. overnight. After cooling to room temperature, the reaction mixture was filtered through kieselguhr and the residue was washed repeatedly with dioxane. The combined filtrates were concentrated to dryness under reduced pressure. The crude product obtained was purified by flash chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1→4:1→1:1). This gave 769 mg (2.42 mmol, 93% content, 82% of theory) of a colorless solid.

Workup

  1. filtrationthe reaction mixture was filtered through kieselguhr
  2. washthe residue was washed repeatedly with dioxane
  3. concentrationThe combined filtrates were concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-759d2be08ba64b498465d47f7e0cbf77
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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