Trimethyl((tributylstannyl)ethynyl)silane → 2-(3,5-Difluoro-4-hydroxyphenyl)-4-ethynylquinolin-6-ol

Participants

Role	Name	HCID	Charge
Reactant	Trimethyl((tributylstannyl)ethynyl)silane	HCID 639663	—
Reactant	4-Bromo-2-(3,5-difluoro-4-hydroxyphenyl)quinolin-6-ol	HCID 135518270	—
Product	2-(3,5-Difluoro-4-hydroxyphenyl)-4-ethynylquinolin-6-ol	HCID 135436566	87%

Reaction Steps

This compound was prepared from 6c following a combination of method J using (trimethylsilylethynyl)tributyltin and method L. Yellow solid; Yield: 87%; mp 220° C. (dec.); 1H-NMR (300 MHz, acetone-d6) δ 4.39 (s, 1H), 7.45 (dd, J=9.1, 2.7 Hz, 1H), 7.60 (d, J=2.7 Hz, 1H), 7.95 (d, J=10.1 Hz, 1H), 7.96 (d, J=7.1 Hz, 1H), 8.00 (d, J=9.2 Hz, 1H), 8.14 (s, 1H), 9.18 (s, 1H), 9.31 (s, 1H); MS (ESI) m/z 296 ([M−H]−), 298 ([M+H]+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07084276B2
Source dataset	uspto-grants-2006_08
ORD ID	ord-03fd43b53d484816aceded56c9677dc8
Source note	uspto-grants-2006_08