4-Fluorophenylboronic acid → HCID 86628188, compound

HRID 420393Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:46])[CH:5]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[C:19]([C:21]2[CH:30]=[CH:29][C:24]3[O:25][CH2:26][CH2:27][O:28][C:23]=3[CH:22]=2)[CH:18]=[C:17](Br)[CH:16]=1)[CH3:7])[CH3:2].[F:47][C:48]1[CH:53]=[CH:52][C:51](B(O)O)=[CH:50][CH:49]=1>>[CH2:1]([O:3][C:4](=[O:46])[CH:5]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:51]2[CH:52]=[CH:53][C:48]([F:47])=[CH:49][CH:50]=2)[CH:18]=[C:19]([C:21]2[CH:30]=[CH:29][C:24]3[O:25][CH2:26][CH2:27][O:28][C:23]=3[CH:22]=2)[CH:20]=1)[CH3:7])[CH3:2]

Participants

Reactant 2

HCID 2856454-Fluorophenylboronic acid

HCID 86628187HCID 86628187, compound

Product 1

HCID 86628188HCID 86628188, compoundYield 34%

Procedure

A similar procedure as described in Example 22, step 2 was used, starting from 4-[3-{6-[3-bromo-5-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-phenoxy]-hexyl}-(2-(2-ethoxycarbonyl-ethyl)-phenoxy)-butyric acid ethyl ester (189 mg, 0.27 mmol) and 4-fluoro-phenylboronic acid (114 mg, 0.82 mmol) to obtain 4-[3-{6-[5-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-4′-fluoro-biphenyl-3-yloxy]-hexyl}-(2-(2-ethoxycarbonyl-ethyl)-phenoxy)-butyric acid ethyl ester (65 mg, 34%) as a light yellow oil: ES(+)-HRMS m/e calculated for C43H49FO8 (M+Na)+ 735.3303, found 735.3298.

Sources & evidence

ORD record: ord-c0ce1f3775164100aca730991595f962
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093385B2

Reaction notes

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