Thiophene-3-boronic acid → 2-(3-Fluoro-4-hydroxyphenyl)-4-thiophen-3-yl-quinolin-6-ol

HRID 7251

Reaction equation

HRID 7251 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.[S:21]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22]1>>[F:20][C:15]1[CH:14]=[C:13]([C:4]2[CH:3]=[C:2]([C:23]3[CH:24]=[CH:25][S:21][CH:22]=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 581760Thiophene-3-boronic acidHCID 1354779434-Bromo-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

Product 1

HCID 1354232712-(3-Fluoro-4-hydroxyphenyl)-4-thiophen-3-yl-quinolin-6-olYield 95%

Procedure

This compound was prepared from 6b using 3-thiopheneboronic acid according to method P. Orange powder; Yield: 95%; mp>160° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 7.06 (t, J=8.8 Hz, 1H), 7.30–7.33 (m, 2H), 7.50 (dd, J=4.9, 1.2 Hz, 1H), 7.82 (dd, J=4.9, 3.0 Hz, 1H), 7.90–7.95 (m, 4H), 8.06 (dd, J=13.0, 2.1 Hz, 1H), 9.97 (s, 1H), 10.19 (s, 1H); MS (ESI) m/z 336 ([M−H]−), 338 ([M+H]+); Anal. Calcd for C19H12FNO2S: C: 67.64, H: 3.59, N: 4.15. Found: C: 66.81, H: 4.14, N: 3.58.

Sources & evidence

ORD record
ord-0e818c8419c54a7fac724398d987ee72
Source dataset
uspto-grants-2006_08
Patent number
US07084276B2

Linked notes

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