3,4-Dichlorobenzeneboronic acid → [4-(3,4-Dichlorophenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Pyridin-2-yl)Methanone

HRID 2104481Notes

Reaction equation

HRID 2104481 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[O:17].[Cl:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][C:30]=1[Cl:31]>>[Cl:24][C:25]1[CH:26]=[C:27]([C:2]2[C:11]3[C:6](=[C:7]([C:12]([F:14])([F:13])[F:15])[CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:17])[CH:28]=[CH:29][C:30]=1[Cl:31]

Participants

3

Reactant 2

HCID 27343303,4-Dichlorobenzeneboronic acidHCID 66913162(4-Chloro-8-trifluoromethyl-quinolin-3-yl)-pyridin-2-yl-methanone

Product 1

HCID 11408234[4-(3,4-Dichlorophenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Pyridin-2-yl)Methanone

Procedure

This compound was prepared using the procedure of Example 1, step 5 using (4-chloro-8-trifluoromethyl-quinolin-3-yl)-pyridin-2-yl-methanone in place of [4-chloro-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone and 3,4-dichlorophenylboronic acid in place of phenyl boronic acid. MS (ESI) m/z 447/449/451 ([M+H]+); 1H NMR (CDCl3) δ 9.22 (s, 1H), 8.52 (d, J=4.6 Hz, 1H), 8.18 (d, J=7.21 Hz, 1H), 7.96 (d, J=7.83 Hz, 1H), 7.84 (m, 2H), 7.61 (m, 1H), 7.42 (m, 3H), 7.13 (dd, J=8.25 and 1.97 Hz, 1H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-94a7592b3efe40cfbf7872c2eed55c15
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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