Formic Acid → HCID 71245375, compound

Participants

Role	Name	HCID	Charge
Reactant	Formic Acid	HCID 284	—
Reactant	Triethylamine	HCID 8471	—
Reactant	2-Quinolinecarboxaldehyde	HCID 79619	—
Reactant	Acetic acid 2-((4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4-aH-8-aza-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester hydrochloride	HCID 67353702	—
Solvent	Acetonitrile	HCID 6342	—
Product	HCID 71245375	HCID 71245375	54.6%

Reaction Steps

A solution of intermediate 6 (200 mg, 0.400 mmol), quinoline-2-carbaldehyde (251 mg, 1.600 mmol), triethylamine (61 mL, 0.440 mmol) and formic acid (263 μL, 3.20 mmol), in acetonitrile (4 ml) is irradiated with microwaves (130° C., 20 minutes). The reaction mixture was partitioned between AcOEt and 5% NaHCO3 solution. The organic layers were then washed with brine, dried over Na2SO4 and filtered. The solvent was evaporated and the crude was purified by silica gel chromatography (DCM/MeOH 99:1) to give compound 11 (132 mg, 54.6% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08710037B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-828265dd02d44998ac5a83cc31223a7d
Source note	uspto-grants-2014_04