(Pyrimidin-5-yl)boronic acid → 2-(3-Fluoro-4-hydroxyphenyl)-4-(5-pyrimidinyl)quinolin-6-ol

HRID 7253

Reaction equation

HRID 7253 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]=[C:25](B(O)O)[CH:24]=[N:23][CH:22]=1>>[F:20][C:15]1[CH:14]=[C:13]([C:4]2[CH:3]=[C:2]([C:25]3[CH:26]=[N:21][CH:22]=[N:23][CH:24]=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 2795193(Pyrimidin-5-yl)boronic acidHCID 1354779434-Bromo-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

Product 1

HCID 1354426282-(3-Fluoro-4-hydroxyphenyl)-4-(5-pyrimidinyl)quinolin-6-olYield 34%

Procedure

This compound was prepared from 6b using 5-pyrimidinylboronic acid according to method P. Yellow powder; Yield: 34%; mp>340° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 7.00 (d, J=2.6 Hz, 1H), 7.08 (t, J=8.8 Hz, 1H), 7.36 (dd, J=9.0, 2.6 Hz, 1 H), 7.98–8.02 (m, 2H), 8.08 (s, 1H), 8.11 (dd, J=13.1, 2.2 Hz, 1H), 9.11 (s, 2H), 9.37 (s, 1H), 10.07 (s, 1H), 10.24 (s, 1H); MS (ESI) m/z 332 ([M−H]−), 334 ([M+H]+); Anal. Calcd for C19H12FN3O2: C: 68.47, H: 3.63, N: 12.61. Found: C: 65.37, H: 3.98, N:11.30.

Sources & evidence

ORD record
ord-bf76c2d6b3c04c949b881161cb4b3370
Source dataset
uspto-grants-2006_08
Patent number
US07084276B2

Linked notes

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