(Pyridin-4-yl)boronic acid → 2-(3-Fluoro-4-hydroxyphenyl)-4-(4-pyridinyl)quinolin-6-ol

HRID 7252Notes

Reaction equation

HRID 7252 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.[N:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>>[F:20][C:15]1[CH:14]=[C:13]([C:4]2[CH:3]=[C:2]([C:24]3[CH:25]=[CH:26][N:21]=[CH:22][CH:23]=3)[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

3

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 1354779434-Bromo-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

Product 1

HCID 1355248852-(3-Fluoro-4-hydroxyphenyl)-4-(4-pyridinyl)quinolin-6-olYield 20%

Procedure

This compound was prepared from 6b using 4-pyridinylboronic acid according to method P. Yellow powder; Yield: 20%; mp>350° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 7.02 (d, J=2.6 Hz, 1H), 7.07 (t, J=8.8 Hz, 1H), 7.34 (dd, J=9.0, 2.6 Hz, 1H), 7.64 (d, J=5.9 Hz, 2H), 7.93 (s, 1H), 7.95–8.00 (m, 2H), 8.08 (dd, J=13.0, 2.1 Hz, 1H), 8.79 (d, J=3.9, 2H), 10.02 (s, 1H), 10.22 (s, 1H); MS (ESI) m/z 331 ([M−H]−), 333 ([M+H]+); Anal. Calcd for C20H13FN2O2: C: 72.28, H: 3.94, N: 8.43. Found: C: 70.79, H: 4.08, N: 7.87.

Sources & evidence

ORD record
ord-2462d807654541a2a1bf0f369b69e9aa
Source dataset
uspto-grants-2006_08
Patent number
US07084276B2

Reaction notes

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