2-(3-Oxobutyl)isoindoline-1,3-dione → 3-{[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(1H-indol-5-yl)-amino]-methyl}-4-fluoro-benzonitrile

Participants

Role	Name	HCID	Charge
Reactant	2-(3-Oxobutyl)isoindoline-1,3-dione	HCID 290728	—
Reactant	4-[(5-Cyano-2-fluoro-benzyl)-(1h-indol-5-yl)-amino]-piperidine-1-carboxylic acid tert-butyl ester	HCID 68972722	—
Product	3-{[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(1H-indol-5-yl)-amino]-methyl}-4-fluoro-benzonitrile	HCID 68970495	—

Reaction Steps

Using general procedure C with the above carbamate (400 mg, 0.891 mmol), then general procedure B with the resulting amine and 2-(3-oxo-butyl)-isoindole-1,3-dione (386 mg, 1.78 mmol) followed by general procedure D afforded 3-{[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(1H-indol-5-yl)-amino]-methyl}-4-fluoro-benzonitrile as a white solid (92 mg, 26% over 3 steps).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07491735B2
Source dataset	uspto-grants-2009_02
ORD ID	ord-413c065e2e8f4bc196869ac20450809d
Source note	uspto-grants-2009_02