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

Participants

Role	Name	HCID	Charge
Reactant	Benzylamine	HCID 7504	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Binap, (A+-)-	HCID 634876	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	6-Bromo-1-isopropyl-3,3-dimethyl-1,3-dihydro-indol-2-one	HCID 90046328	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	6-(Benzylamino)-1-isopropyl-3,3-dimethylindolin-2-one	HCID 90047703	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09221816B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-5151a38d76b04f15b799e418c7f59db9
Source note	uspto-grants-2015_12