4-(Trifluoromethyl)phenylboronic acid → HCID 90410123, compound

HRID 1848760Notes

Reaction equation

Br[C:2]1[CH:34]=[CH:33][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([O:16][CH2:17][C:18]4[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=4)[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:24][C:25]([CH2:31][CH3:32])([CH2:29][CH3:30])[C:26]([OH:28])=[O:27])=[C:4](F)[CH:3]=1.[F:36][C:37]([F:48])([F:47])[C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1.FC(F)(F)C1C=CC(B(O)O)=CC=1>>[CH2:29]([C:25]([CH2:24][C:8]1[N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([C:41]3[CH:42]=[CH:43][C:38]([C:37]([F:48])([F:47])[F:36])=[CH:39][CH:40]=3)=[CH:34][CH:33]=2)[C:11]2[CH:12]=[C:13]([O:16][CH2:17][C:18]3[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=3)[CH:14]=[CH:15][C:10]=2[N:9]=1)([CH2:31][CH3:32])[C:26]([OH:28])=[O:27])[CH3:30]

Participants

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acid

HCID 90411039HCID 90411039, compound

Product 1

HCID 90410123HCID 90410123, compound

Procedure

The title compound was prepared using analogous conditions described in Example 144 using (4-(trifluoromethyl)phenyl)boronic acid 2-((1-(4-bromo-2-fluorobenzyl)-6-((1-methyl-1H-pyrazol-3-yl)methoxy)-1H-benzo[d]imidazol-2-yl)methyl)-2-ethylbutanoic acid and (4-(trifluoromethyl)phenyl)boronic acid. MS (ESI): mass calcd. for C33H32F4N4O3, 608.24; m/z found, 609.2 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 7.81 (d, J=8.3, 2H), 7.73 (d, J=8.4, 2H), 7.57-7.54 (m, 1H), 7.54-7.52 (m, 1H), 7.49 (d, J=2.3, 1H), 7.41 (dd, J=8.0, 1.8, 1H), 7.03 (d, J=2.3, 1H), 6.93 (dd, J=8.8, 2.3, 1H), 6.88 (t, J=7.9, 1H), 6.28 (d, J=2.3, 1H), 5.61 (s, 2H), 5.01 (s, 2H), 3.81 (s, 3H), 3.12 (s, 2H), 1.90-1.73 (m, 4H), 0.88 (t, J=7.5, 6H).

Sources & evidence

ORD record: ord-2fd3f01da8a640beb0b07eee2b558f08
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952177B2

Reaction notes

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