(4-Methoxyphenyl)boronic acid → HCID 86628193, compound

HRID 420398Notes

Reaction equation

HRID 420398 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[C:22](=[O:30])[N:23]([CH3:29])[C:24](=[O:28])[N:25]([CH3:27])[CH:26]=2)[CH:18]=[C:17](Br)[CH:16]=1)[CH3:7])[CH3:2].[CH3:47][O:48][C:49]1[CH:54]=[CH:53][C:52](B(O)O)=[CH:51][CH:50]=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:52]2[CH:53]=[CH:54][C:49]([O:48][CH3:47])=[CH:50][CH:51]=2)[CH:18]=[C:19]([C:21]2[C:22](=[O:30])[N:23]([CH3:29])[C:24](=[O:28])[N:25]([CH3:27])[CH:26]=2)[CH:20]=1)[CH3:7])[CH3:2]

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 68746208HCID 68746208, compound

Product 1

HCID 86628193HCID 86628193, compoundYield 45%

Procedure

A similar procedure as described in Example 1, step 2 was used, starting from 4-[3-{6-[3-bromo-5-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl) -phenoxy]-hexyl}-(2-(2-ethoxycarbonyl-ethyl)-phenoxy)-butyric acid ethyl ester (130 mg, 0.18 mmol) and 4-methoxyphenylboronic acid (85 mg, 0.56 mmol) to obtain 4-[3-{6-[5-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4′-methoxy-biphenyl-3-yloxy]-hexyl}-(2-(2-ethoxycarbonyl-ethyl)-phenoxy)-butyric acid ethyl ester (59 mg, 44%) as a light yellow oil: ES(+)-HRMS m/e calculated for C42H52N2O9 (M+H)+ 729.3746, found 729.3742.

Sources & evidence

ORD record
ord-08c695139b634199a046c75ade0296da
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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