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

HRID 7243Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[C:17]([F:19])[C:16]([OH:20])=[C:15]([F:21])[CH:14]=2)[CH:3]=1.C[Si]([C:26]#[C:27][Sn](CCCC)(CCCC)CCCC)(C)C>>[F:21][C:15]1[CH:14]=[C:13]([C:4]2[CH:3]=[C:2]([C:26]#[CH:27])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=3)[N:5]=2)[CH:18]=[C:17]([F:19])[C:16]=1[OH:20]

Participants

Reactant 2

HCID 639663Trimethyl((tributylstannyl)ethynyl)silane

HCID 1355182704-Bromo-2-(3,5-difluoro-4-hydroxyphenyl)quinolin-6-ol

Product 1

HCID 1354365662-(3,5-Difluoro-4-hydroxyphenyl)-4-ethynylquinolin-6-olYield 87%

Procedure

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]+).

Sources & evidence

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

Reaction notes

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