Diisopropylethylamine → (S)-1-(1-Methyl-1H-indol-4-yloxy)-3-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-propan-2-ol

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(2S)-Glycidyl 1-methylindol-4-yl ether	HCID 59686815	—
Reactant	Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene	HCID 59686818	—
Solvent	Ethanol	HCID 702	—
Product	(S)-1-(1-Methyl-1H-indol-4-yloxy)-3-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-propan-2-ol	HCID 69233735	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

(S)-1-Methyl-4-oxiranylmethoxy-1H-indole (50 mg, 0.25 mmol) and Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene (50 mg, 0.189 mmol) were placed in a μW tube with ethanol (2 ml), DIPEA (100 μL, 0.576 mmol) and heated to 120° C. for 900 sec. The solvent was evaporated from the reaction mixture and the residue was purified via flash chromatography (gradient 30% to 100% ethyl acetate/heptane) to yield the title compound as a residue.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08530475B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-ddd004fecaf94130b2abbe57112a1163
Source note	uspto-grants-2013_09