4-Cyanophenylboronic acid → HCID 135427962, compound

HRID 899165Notes

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.[C:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)#[N:23]>>[C:22]([C:24]1[CH:29]=[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]=1)#[N:23]

Participants

Reactant 2

HCID 27343264-Cyanophenylboronic acid

HCID 135520118HCID 135520118, compound

Product 1

HCID 135427962HCID 135427962, compoundYield 96%

Procedure

This compound was prepared from 7-bromo-3,9-dihydroxy-6H-chromeno[4,3-b]quinoline (7) using 4-cyanophenylboronic acid according to method M. Ivory powder; Yield: 96%; mp 295° C. (dec.); 1H-NMR (400 MHz, DMSOd-6) δ 4.99 (s, 2H), 6.36 (d, J=2.3 Hz, 1H), 6.53 (d, J=2.7 Hz, 1H), 6.61 (dd, J=8.7, 2.3 Hz, 1H), 7.27 (dd, J=9.1, 2.6 Hz, 1H), 7.62 (d, J=8.5 Hz, 2H), 7.91 (d, J=9.0 Hz, 2H), 8.09 (d, J=8.3 Hz, 1H), 8.16 (d, J=8.6 Hz, 1H), 9.86 (s, 1H), 9.99 (s, 1H); MS (ESI) m/z 365 ([M−H]−), 367 ([M+H]+); HRMS (ESI+) calcd for C23H14N2O3 367.1077 ([M+H]30 ). Found: 367.1074.

Sources & evidence

ORD record: ord-0f637ce98c624e0fab0eb63c0273420b
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354927B2

Reaction notes

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