Boron tribromide → 2-Ethyl-6-[2-(3-hydroxy-pyrrol idine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-benzofuran-3-carboxylic acid methylamide

Participants

Role	Name	HCID	Charge
Reactant	Boron tribromide	HCID 25134	—
Reactant	2-Ethyl-6-[2-(3-methoxypyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]benzofuran-3-carboxylic acid methylamide	HCID 10345050	—
Reactant	6-Hydroxy-n,2-dimethyl-1-benzothiophene-3-carboxamide	HCID 20767863	—
Product	2-Ethyl-6-[2-(3-hydroxy-pyrrol idine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-benzofuran-3-carboxylic acid methylamide	HCID 20767790	—

Reaction Steps

This material was prepared from 2-ethyl-6-[2-(3-methoxypyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]benzofuran-3-carboxylic acid methylamide 14 by treatment with BBr3 in a manner as previously described for 1d. 1H NMR (DMSO-d6) δ 8.56 (1H, d, J=5.3 Hz), 8.07(1H, s), 8.00 (1H, d, J=4.1 Hz), 7.82 (1H, d, J=8.6 Hz), 7.68 (1H, d, J=2.0 Hz), 7.25 (1H, dd, J=8.6, 2.0 Hz), 6.73 (1H, d, J=5.3 Hz), 5.07 (1H, t, J=3.5 Hz), 4.35 (1H, m), 3.97 (1H, m), 3.86–3.46 (3H, m), 3.03 (2H, q, J=7.6 Hz), 2.80 (3H, d, J=4.5 Hz), 2.10–1.80 (2H, m), 1.27 (3H, t, J=7.6 Hz).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07045528B2
Source dataset	uspto-grants-2006_05
ORD ID	ord-f7e63e954d864fa0a32c0c04865dd192
Source note	uspto-grants-2006_05