(3-Methoxyphenyl)boronic acid → HCID 135438509, compound

HRID 899169Notes

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]2[C:13]3[C:18]([O:19][CH2:20][C:3]=12)=[CH:17][C:16]([OH:21])=[CH:15][CH:14]=3.[CH3:22][O:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1>>[OH:21][C:16]1[CH:17]=[C:18]2[O:19][CH2:20][C:3]3[C:4](=[N:5][C:6]4[C:11]([C:2]=3[C:28]3[CH:27]=[CH:26][CH:25]=[C:24]([O:23][CH3:22])[CH:29]=3)=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=4)[C:13]2=[CH:14][CH:15]=1

Participants

Reactant 2

HCID 2734370(3-Methoxyphenyl)boronic acid

HCID 135520118HCID 135520118, compound

Product 1

HCID 135438509HCID 135438509, compoundYield 87%

Procedure

This compound was prepared from 7-bromo-3,9-dihydroxy-6H-chromeno[4,3-b]quinoline (7) using 3-methoxyphenylboronic acid according to method M. Yellow powder; Yield: 87%; mp 155-158° C. (dec.); 1H-NMR (400 MHz, DMSOd-6) δ 3.82 (s, 3H), 4.99 (d, J=14.2 Hz, 1H), 5.04 (d, J=14.2 Hz, 1H), 6.35 (d, J=2.3 Hz, 1H), 6.60 (dd, J=8.6, 2.3 Hz, 1H), 6.71 (d, J=2.7 Hz, 1H), 6.90 (m, 1H), 6.92 (d, J=1.6 Hz, 1H), 7.12 (m, 1H), 7.24 (dd, J=9.1, 2.7 Hz, 1H), 7.52 (dd, J=8.2, 7.9 Hz, 1H), 7.89 (d, J=9.1 Hz, 1H), 8.15 (d, J=8.6 Hz, 1H), 9.80 (s, 1H), 9.96 (s, 1H); MS (ESI) m/z 370 ([M−H]−), 372 ([M+H]+); HRMS (ESI+) calcd for C23H17NO4372.1230 ([M+H]+). Found: 372.1223.

Sources & evidence

ORD record: ord-73111c4863254c248ebc7e6910c9c7f6
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354927B2

Reaction notes

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