Trimethyl((tributylstannyl)ethynyl)silane → 2-(3-Fluoro-4-hydroxyphenyl)-4-[(trimethylsilyl)ethynyl]quinolin-6-ol

HRID 7242Notes

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]=[CH:17][C:16]([OH:19])=[C:15]([F:20])[CH:14]=2)[CH:3]=1.[CH3:21][Si:22]([C:25]#[C:26][Sn](CCCC)(CCCC)CCCC)([CH3:24])[CH3:23]>>[F:20][C:15]1[CH:14]=[C:13]([C:4]2[CH:3]=[C:2]([C:26]#[C:25][Si:22]([CH3:24])([CH3:23])[CH3:21])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=3)[N:5]=2)[CH:18]=[CH:17][C:16]=1[OH:19]

Participants

Reactant 2

HCID 639663Trimethyl((tributylstannyl)ethynyl)silane

HCID 1354779434-Bromo-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

Product 1

HCID 1355084302-(3-Fluoro-4-hydroxyphenyl)-4-[(trimethylsilyl)ethynyl]quinolin-6-olYield 94%

Procedure

This compound was prepared from 6b and (trimethylsilylethynyl)tributyltin according to method J. Red powder; Yield: 94%; 1H-NMR (300 MHz, acetone-d6) δ 0.43 (s, 9H), 7.21 (dd, J=8.8, 8.8 Hz, 1H), 7.51 (dd, J=9.1, 2.7 Hz, 1H), 7.68 (d, J=2.7 Hz, 1H), 8.05 (m, 1H), 8.07 (d, J=9.0 Hz, 1H), 8.13 (s, 1H), 8.18 (dd, J=12.8, 2.1 Hz, 1H), 9.05 (s, 1H), 9.26 (s, 1H); MS (ESI) m/z 350 ([M−H]−), 352 ([M+H]+).

Sources & evidence

ORD record: ord-9fbcc659dc29475ebabf18f9a67dbd15
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084276B2

Reaction notes

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