Trimethyl((tributylstannyl)ethynyl)silane → 8-Chloro-4-ethynyl-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

HRID 1867496Notes

Reaction equation

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

Participants

Reactant 2

HCID 639663Trimethyl((tributylstannyl)ethynyl)silane

HCID 1354446414-Bromo-8-chloro-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

Product 1

HCID 1355453758-Chloro-4-ethynyl-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-olYield 73%

Procedure

This compound was prepared from 45a following a combination of method J using (trimethylsilylethynyl)tributyltin and method L. Yellow solid; Yield: 73%; mp 210° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 5.06 (s, 1H), 7.09 (dd, J=8.9, 8.8 Hz, 1H), 7.45 (d, J=2.6 Hz, 1H), 7.56 (d, J=2.6 Hz, 1H), 8.00 (dd, J=8.5, 1.7 Hz, 1H), 8.12 (dd, J=12.9, 2.2 Hz, 1H), 8.26 (s, 1H), 10.34 (s, 1H), 10.60 (s, 1H); 19F-NMR (400 MHz, DMSO-d6) δ −136.30 (dd, J=13.2, 9.3 Hz); MS (ESI) m/z 312/314 ([M−H]−), 314/316 ([M+H]+); Anal. Calcd for C17H9ClFNO2: C, 65.09; H, 2.89; N, 4.46. Found: C, 64.86; H, 3.14; N, 4.05.

Sources & evidence

ORD record: ord-97b5b8d944484e8f9b9abf57151aad71
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632845B2

Reaction notes

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