Benzylamine → HCID 90047497, compound

HRID 1507563Notes

Reaction equation

HRID 1507563 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][C:3]=1[F:15].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:62]([NH2:69])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1.C(OCC)(=O)C.O.C([O-])([O-])=O.[Na+].[Na+].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]>[CH2:62]([NH:69][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][C:3]=1[F:15])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1

Participants

10

Reactant 4

HCID 7504BenzylamineHCID 634876Binap, (A+-)-HCID 2733832Lithium HexamethyldisilazideHCID 90047373HCID 90047373, compound

Product 1

HCID 90047497HCID 90047497, compound

Reagents, catalysts & solvents 5

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-bromo-5-fluoro-1,3,3-trimethylindolin-2-one (2.8 g, 10.3 mmol) in tetrahydrofuran (280 ml) under an argon atmosphere were added 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (320 mg, 514 μmol), tris(dibenzylideneacetone)dipalladium(0) (471 mg, 514 μmol), benzylamine (2.21 g, 2.25 ml, 20.6 mmol) and a 1 M solution of lithium bis(trimethylsilyl)amide (25.7 ml, 25.7 mmol). The reaction mixture was heated to 80° C. in the microwave for 45 minutes and then diluted with ethyl acetate, water and 2 N aqueous Na2CO3 solution. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate. The solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/heptane as eluent. The title compound was obtained as light yellow powder (1.57 g).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-56c458b0f4764755ace214098901b2c7
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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