(S)-6-(N-(2-(benzyloxy)but-3-enyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide → (S)-7-Benzyloxy-2-(4-fluoro-phenyl)-9-methanesulfonyl-5-methyl-8,9-dihydro-7H-1-oxa-9,10-diaza-cyclohepta[f]indene-3-carboxylic acid methylamide

https://huagongshe.com/reaction/2190178

Participants

Role	Name	HCID	Charge
Reactant	(S)-6-(N-(2-(benzyloxy)but-3-enyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide	HCID 54575747	—
Catalyst	(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)ruthenium	HCID 11763533	—
Solvent	Toluene	HCID 1140	—
Product	(S)-7-Benzyloxy-2-(4-fluoro-phenyl)-9-methanesulfonyl-5-methyl-8,9-dihydro-7H-1-oxa-9,10-diaza-cyclohepta[f]indene-3-carboxylic acid methylamide	HCID 66664425	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of (S)-6-(N-(2-(benzyloxy)but-3-enyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide (543 mg, 0.963 mmol) in toluene is added Hoveyda-Grubbs 2nd generation catalyst (6 mg, 0.0096 mmol), and the reaction mixture is heated to 100° C. for 18 h. After the reaction is judged complete by LCMS, the toluene is removed in vacuo, and the solid is triturated with methanol to afford (S)-7-Benzyloxy-2-(4-fluoro-phenyl)-9-methanesulfonyl-5-methyl-8,9-dihydro-7H-1-oxa-9,10-diaza-cyclohepta[f]indene-3-carboxylic acid methylamide that is taken directly to the next step.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08324239B2
Source dataset	uspto-grants-2012_12
ORD ID	ord-58d8854e7fa14ed5ac8d5b161c4dc1b1
Source note	uspto-grants-2012_12