Dichloromethane → (7bR,11aS)-N-[2-Ethoxy-3-pyridinyl]-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-6-amine, bis hydrochloride salt

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	3-Bromo-2-ethoxypyridine	HCID 10987308	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H) carboxylate	HCID 86586437	—
Catalyst	Palladium	HCID 23938	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	(7bR,11aS)-N-[2-Ethoxy-3-pyridinyl]-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-6-amine, bis hydrochloride salt	HCID 131724731	—

Reaction Steps

Following the procedures described in Example 175 and using 3-bromo-2-ethoxypyridine, sodium tert-butoxide as the base and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II), complex with dichloromethane, as the palladium source, tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)-carboxylate from Example 33, Part B was converted into the title compound of Example 186 as a solid. ESI MS m/z 383.2 [C21H26N4OS+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06849619B2
Source dataset	uspto-grants-2005_02
ORD ID	ord-6ab698a3457d407d84690cf4ec0f1a57
Source note	uspto-grants-2005_02