Benzylamine → 6-(Benzylamino)-1-isopropyl-3,3-dimethylindolin-2-one

HRID 1507576Notes

Reaction equation

HRID 1507576 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:16])([CH3:15])[C:7](=[O:14])[N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+].[CH2:69]([NH2:76])[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.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.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH2:69]([NH:76][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:16])([CH3:15])[C:7](=[O:14])[N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1)[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 10340Sodium CarbonateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 900463286-Bromo-1-isopropyl-3,3-dimethyl-1,3-dihydro-indol-2-one

Product 1

HCID 900477036-(Benzylamino)-1-isopropyl-3,3-dimethylindolin-2-one

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-bromo-1-isopropyl-3,3-dimethylindolin-2-one (1.99 g, 7.08 mmol, 70%) in THF (20.0 ml) was added BINAP (227 mg, 354 μmol) and sodium tert-butoxide (1.74 g, 17.7 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (378 mg, 354 μmol) and benzylamine (766 mg, 782 μl, 7.08 mmol) under an argon atmosphere. The reaction mixture was heated to 70° C. for 18 hours. An aqueous solution of Na2CO3 was added to the reaction mixture at room temperature, the aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were 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 yellow foam (1.60 g).

Workup

  1. extractionthe aqueous phase was extracted with tert-butyl methyl ether
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. customthe solvent was evaporated
  4. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-5151a38d76b04f15b799e418c7f59db9
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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