Formaldehyde → Isopropyl 2-(1,2,3,4-tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetate

Participants

Role	Name	HCID	Charge
Reactant	Formaldehyde	HCID 712	—
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	Ethyl bromoacetate	HCID 7748	—
Reactant	4-Methylphenylhydrazine monohydrochloride	HCID 12504	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	4,4-Diethoxy-N-methylbutan-1-amine	HCID 13994547	—
Reactant	2-(1,2,3,4-Tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetic acid	HCID 44242645	—
Reactant	Ethyl 2-(1-p-tolylhydrazinyl)acetate	HCID 57930412	—
Reactant	ethyl 2-(5-methyl-3-(2-(methylamino)ethyl)-1H-indol-1-yl)acetate	HCID 57930443	—
Solvent	Isopropanol	HCID 3776	—
Solvent	Acetonitrile	HCID 6342	—
Solvent	Triethylamine	HCID 8471	—
Solvent	Sodium Hydroxide	HCID 14798	—
Solvent	Ethyl 2-(1,2,3,4-tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetate	HCID 57930374	—
Product	Isopropyl 2-(1,2,3,4-tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetate	HCID 57930407	—

Reaction Steps

The title compound is prepared by following General Methods 1, 3, 4, 5 and 6 by using p-tolylhydrazine hydrochloride, ethyl bromoacetate, and triethylamine (General Method 1), ethyl 2-(1-(4-methylphenyl)hydrazinyl)acetate and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3), ethyl 2-(5-methyl-3-(2-(methylamino)ethyl)-1H-indol-1-yl)acetate, formaldehyde and TFA in acetonitrile (General Method 4), ethyl 2-(6-methyl-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetate and NaOH (General Method 5), and 2-(6-methyl-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetic acid, isopropanol and EDCI (General Method 6).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09260429B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-c278a0d909dd41dda2b9612981f3d826
Source note	uspto-grants-2016_02