4-(Trifluoromethyl)phenylboronic acid → HCID 135446024, compound

HRID 899167Notes

Reaction equation

HRID 899167 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.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=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:27]3[CH:28]=[CH:29][C:24]([C:23]([F:34])([F:33])[F:22])=[CH:25][CH:26]=3)=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=4)[C:13]2=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 135520118HCID 135520118, compound

Product 1

HCID 135446024HCID 135446024, compoundYield 95%

Procedure

This compound was prepared from 7-bromo-3,9-dihydroxy-6H-chromeno[4,3-b]quinoline (7) using 4-trifluoromethylphenylboronic acid according to method M. Yellow powder; Yield: 95%; mp 175-177° C. (dec.); 1H-NMR (400 MHz, DMSOd-6) δ 5.00 (s, 2H), 6.36 (d, J=2.3 Hz, 1H), 6.56 (d, J=2.6 Hz, 1H), 6.61 (dd, J=8.6, 2.2 Hz, 1H), 7.26 (dd, J=9.1, 2.6 Hz, 1H), 7.64 (d, J=7.9 Hz, 2H), 7.92 (d, J=9.0 Hz, 1H), 7.98 (d, J=8.1 Hz, 2H), 8.16 (d, J=8.6 Hz, 1H), 9.84 (s, 1H), 10.00 (s, 1H); 19F-NMR (400 MHz, DMSOd-6) δ −61.43 (s); MS (ESI) m/z 408 ([M−H]−), 410 ([M+H]+); HRMS (ESI+) calcd for C23H14F3NO3 410.0999 ([M+H]+). Found: 410.0992.

Sources & evidence

ORD record
ord-08f2dc27af454937bb07284e7e9f379e
Source dataset
uspto-grants-2008_04
Patent number
US07354927B2

Reaction notes

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