Tributylvinyltin → 8-Chloro-2-(3-fluoro-4-hydroxyphenyl)-4-vinylquinolin-6-ol

HRID 7257

반응식

HRID 7257 반응식
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.[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC>>[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[CH:22]=[CH2:23]

참가 물질

3

반응물 2

HCID 81998TributylvinyltinHCID 1354446414-Bromo-8-chloro-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

생성물 1

HCID 1354365838-Chloro-2-(3-fluoro-4-hydroxyphenyl)-4-vinylquinolin-6-ol수율 84%

실험 절차

This compound was prepared from 45a based on method J using 1.1 equiv. of tributyl(vinyl)tin at 90° C. Red solid; Yield: 84%; mp 225° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 5.74 (dd, J=11.1, 1.0 Hz, 1H), 6.30 (dd, J=17.3, 1.1 Hz, 1H), 7.10 (dd, J=8.8, 8.8 Hz, 1H), 7.35 (d, J=2.6 Hz, 1H), 7.38 (dd, J=17.3, 11.1 Hz, 1H), 7.53 (d, J=2.5 Hz, 1H), 8.04 (dd, J=8.4, 1.7 Hz, 1H), 8.16 (dd, J=13.1, 2.1 Hz, 1H), 8.16 (s, 1H), 10.27 (s, 1H), 10.35 (s, 1H); 19F-NMR (400 MHz, DMSO-d6) δ −136.51 (dd, J=13.2, 9.3 Hz); MS (ESI) m/z 314/316 ([M−H]−), 316/318 ([M+H]+); Anal. Calcd for C17H11ClFNO2: C: 64.67, H: 3.51, N: 4.44. Found: C: 63.57, H: 3.61, N: 4.04.

후처리

  1. customat 90° C

출처 및 근거

ORD 기록
ord-d2ccbacffcae40e28a57686d20464e40
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084276B2

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