(3-Chlorophenyl)boronic acid → HCID 135399711, compound

HRID 899168Notes

Reaction equation

HRID 899168 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.[Cl:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1>>[Cl:22][C:23]1[CH:28]=[C:27]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=3)[N:5]=[C:4]3[C:13]4[C:18]([O:19][CH2:20][C:3]=23)=[CH:17][C:16]([OH:21])=[CH:15][CH:14]=4)[CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 135520118HCID 135520118, compound

Product 1

HCID 135399711HCID 135399711, compoundYield 94%

Procedure

This compound was prepared from 7-bromo-3,9-dihydroxy-6H-chromeno[4,3-b]quinoline (7) using 3-chlorophenylboronic acid according to method M. Orange powder; Yield: 94%; mp 162-165° C. (dec.); 1H-NMR (400 MHz, DMSOd-6) δ 5.01 (s, 2H), 6.36 (d, J=2.3 Hz, 1H), 6.60 (dd, J=8.5, 2.2 Hz, 1H), 6.61 (d, J=2.6 Hz, 1H), 7.26 (dd, J=9.1, 2.6 Hz, 1H), 7.35 (m, 1H), 7.50 (d, J=1.0 Hz, 1H), 7.64 (dd, J=3.9, 1.6, Hz, 2H), 7.90 (d, J=9.1 Hz, 1H), 8.15 (d, J=8.8 Hz, 1H), 9.86 (s, 1H), 9.98 (s, 1H); MS (ESI) m/z 374/376 ([M−H]−), 376/378 ([M+H]+); HRMS (ESI+) calcd for C22H14ClNO3 376.0735 ([M+H]+). Found: 376.0721.

Sources & evidence

ORD record
ord-37d9946100b54a58befd977b131f1486
Source dataset
uspto-grants-2008_04
Patent number
US07354927B2

Reaction notes

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