4-(Trifluoromethyl)phenylboronic acid → HCID 86268900, compound

HRID 1848746Notes

Reaction equation

HRID 1848746 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:15]1[CH:16]=[C:17]([CH:46]=[CH:47][CH:48]=1)[CH2:18][N:19]1[C:23]2[CH:24]=[C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][N:31]=3)[CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[C@H:37]1[CH2:42][CH2:41][CH2:40][CH2:39][C@H:38]1[C:43]([OH:45])=[O:44]>>[CH3:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][O:28][C:25]2[CH:26]=[CH:27][C:22]3[N:21]=[C:20]([C@H:37]4[CH2:42][CH2:41][CH2:40][CH2:39][C@H:38]4[C:43]([OH:45])=[O:44])[N:19]([CH2:18][C:17]4[CH:46]=[C:47]([C:6]5[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=5)[CH:48]=[CH:15][CH:16]=4)[C:23]=3[CH:24]=2)=[N:31][CH:32]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 90411200HCID 90411200, compound

Product 1

HCID 86268900HCID 86268900, compound

Procedure

The title compound was prepared using similar methods to those in Example 144 using (4-(trifluoromethyl)phenyl)boronic acid and racemic cis-2-{1-(3-bromobenzyl)-6-[(5-methylpyridin-2-yl)methoxy]-1H-benzimidazol-2-yl}cyclohexanecarboxylic acid. MS (ESI): mass calcd. for C35H32F3N3O3, 599.24; m/z found, 600.2 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.32 (d, J=2.0 Hz, 1H), 7.68 (d, J=8.1 Hz, 2H), 7.62 (d, J=8.8 Hz, 1H), 7.57 (d, J=8.1 Hz, 2H), 7.54 (d, J=7.8 Hz, 1H), 7.45 (dd, J=8.1, 2.2 Hz, 1H), 7.43-7.38 (m, 2H), 7.35 (d, J=8.0 Hz, 1H), 7.04 (dd, J=8.8, 2.3 Hz, 1H), 6.97 (d, J=7.8 Hz, 1H), 6.82 (d, J=2.3 Hz, 1H), 5.36 (s, 2H), 5.14 (s, 2H), 3.25-3.09 (m, 1H), 3.09-2.97 (m, 1H), 2.65-2.53 (m, 1H), 2.28 (s, 3H), 1.87-1.71 (m, 3H), 1.70-1.58 (m, 2H), 1.51-1.31 (m, 2H).

Sources & evidence

ORD record
ord-6459029343714f99989d54c01dfc69bb
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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