3,4-Difluorobenzeneboronic acid → HCID 90415215, compound

HRID 1776749Notes

Reaction equation

Br[C:2]1[CH:38]=[CH:37][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][C:14]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:15][C:10]=3[N:9]=[C:8]2[C@@H:28]2[C@H:30]([C:31]([O:33]C)=[O:32])[C:29]2([CH3:36])[CH3:35])=[C:4]([F:39])[CH:3]=1.[F:40][C:41]1[CH:42]=[C:43](B(O)O)[CH:44]=[CH:45][C:46]=1[F:47]>>[CH3:35][C:29]1([CH3:36])[C@H:28]([C:8]2[N:7]([CH2:6][C:5]3[CH:37]=[CH:38][C:2]([C:44]4[CH:43]=[CH:42][C:41]([F:40])=[C:46]([F:47])[CH:45]=4)=[CH:3][C:4]=3[F:39])[C:11]3[CH:12]=[CH:13][C:14]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:15][C:10]=3[N:9]=2)[C@@H:30]1[C:31]([OH:33])=[O:32]

Participants

Reactant 2

HCID 27343373,4-Difluorobenzeneboronic acid

HCID 90415632HCID 90415632, compound

Product 1

HCID 90415215HCID 90415215, compound

Procedure

The title compound was prepared using similar methods to those in Example 97 using racemic methyl cis-3-[1-(4-bromo-2-fluorobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]-2,2-dimethylcyclopropanecarboxylate and (3,4-difluorophenyl)boronic acid in Step A. MS (ESI): mass calcd. for C36H28F3N3O3, 607.21; m/z found, 608.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.20 (d, J=8.5, 1H), 8.11 (d, J=8.5, 1H), 7.83 (d, J=8.2, 1H), 7.76-7.72 (m, 1H), 7.68 (d, J=8.5, 1H), 7.58-7.54 (m, 1H), 7.35-7.20 (m, 7H), 7.14-7.11 (m, 1H), 6.93-6.88 (m, 1H), 5.46 (d, J=17, 1H), 5.43 (s, 2H), 5.41 (d, J=17, 1H), 2.34 (d, J=8.2, 1H), 2.13 (d, J=8.2, 1H), 1.31 (s, 3H), 1.05 (s, 3H).

Sources & evidence

ORD record: ord-9bbe808527de4c11802bcd46a85eeba3
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265770B2

Reaction notes

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