4-(Trifluoromethyl)phenylboronic acid → HCID 90414656, compound

HRID 1776754Notes

Reaction equation

HRID 1776754 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:52]=[CH:51][C:18]([CH2:19][N:20]2[C:24]3[CH:25]=[CH:26][C:27]([O:29][CH2:30][C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][CH:35]=[C:36]([F:41])[CH:37]=5)[N:32]=4)=[CH:28][C:23]=3[N:22]=[C:21]2[CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH:43]2[C:48]([OH:50])=[O:49])=[CH:17][CH:16]=1.CC1(C)C(C)(C)OB(C2N=CSC=2)O1>>[F:41][C:36]1[CH:37]=[C:38]2[C:33](=[CH:34][CH:35]=1)[N:32]=[C:31]([CH2:30][O:29][C:27]1[CH:26]=[CH:25][C:24]3[N:20]([CH2:19][C:18]4[CH:17]=[CH:16][C:15]([C:6]5[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=5)=[CH:52][CH:51]=4)[C:21]([C@H:42]4[CH2:47][CH2:46][CH2:45][CH2:44][C@H:43]4[C:48]([OH:50])=[O:49])=[N:22][C:23]=3[CH:28]=1)[CH:40]=[CH:39]2

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 131733026HCID 131733026, compound

Product 1

HCID 90414656HCID 90414656, compound

Procedure

The title compound was prepared using similar methods to those in Example 97 using (4-(trifluoromethyl)phenyl)boronic acid and racemic (1R,2S)-2-(1-(4-bromobenzyl)-5-((6-fluoroquinolin-2-yl)methoxy)-1H-benzo[d]imidazol-2-yl)cyclohexanecarboxylic acid-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole in Step A. MS (ESI): mass calcd. for C38H31F4N3O3, 653.23; m/z found, 654.2 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.33 (d, J=8.4, 1H), 8.11-8.05 (m, 1H), 7.81-7.74 (m, 3H), 7.70 (d, J=8.3, 2H), 7.66-7.56 (m, 4H), 7.30 (d, J=2.4, 1H), 7.27-7.22 (m, 3H), 7.02 (dd, J=8.8, 2.4, 1H), 5.60 (d, J=17.1, 1H), 5.54 (d, J=17.2, 1H), 5.39 (s, 2H), 3.65-3.55 (m, 1H), 2.90-2.80 (m, 1H), 2.42-2.31 (m, 1H), 2.08-1.98 (m, 1H), 1.92-1.73 (m, 4H), 1.54-1.38 (m, 2H).

Sources & evidence

ORD record
ord-c88b2c867dcf48dca84d57984aae11bf
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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