Nitrogen → tert-Butyl 3-(chloromethyl)indoline-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	Tributylstannane	HCID 5948	—
Reactant	Azobisisobutyronitrile	HCID 6547	—
Reactant	2-Bromo-N-(tert-butyloxycarbonyl)-N-(3-chloro-2-propen-1-yl) aniline	HCID 72429334	—
Solvent	Toluene	HCID 1140	—
Product	tert-Butyl 3-(chloromethyl)indoline-1-carboxylate	HCID 58805418	59%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A solution of 3.3 (110 mg, 0.318 mmol) and AIBN (21 mg, 0.127 mmol) in dry toluene (10 ml) was degassed for 15 mins with N2 and then heated to 90° C. Bu3SnH (84 μl, 0.318 mmol) was added to the mixture in four portions over an hour and the resulting mixture was stirred at 90° C. for a further 2 h. The mixture was then concentrated and purified by flash chromatography (SiO2, 0–10% EtOAc in hexane) to afford 3.4 (50 mg, 59%) as a colourless oil.FAB MS: (NBA/NaI) 267, (M+H+, expected 267) 292 (M+Na+, expected 292).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07179921B2
Source dataset	uspto-grants-2007_02
ORD ID	ord-318d9f17868242d896b68064fd8083d3
Source note	uspto-grants-2007_02