Phenylboronic Acid → 4-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(5-thiophen-3-yl-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid ethyl ester

HRID 420370Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:41])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([C:28]3[CH:32]=[CH:31][S:30][CH:29]=3)[CH:25]=[C:24](I)[CH:23]=2)[C:10]=1[CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH3:2].[C:42]1(B(O)O)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[CH2:1]([O:3][C:4](=[O:41])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:25]=[C:26]([C:28]3[CH:32]=[CH:31][S:30][CH:29]=3)[CH:27]=2)[C:10]=1[CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH3:2]

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 575865384-{3-[6-(3-Iodo-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester

Product 1

HCID 575864454-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(5-thiophen-3-yl-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid ethyl esterYield 55.2%

Procedure

A similar procedure as described in Example 12, step 8 was used, starting from 4-{3-[6-(3-iodo-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (216 mg, 0.31 mmol) and phenylboronic acid (152 mg, 1.25 mmol) to give 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(5-thiophen-3-yl-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid ethyl ester (110 mg, 55%) as a colorless oil: ES(+)-HRMS m/e calculated for C39H46O6S (M+Na)+ 665.2907, found 665.2907.

Sources & evidence

ORD record: ord-10220a4b5d99444d8bf9e964359c033b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093385B2

Reaction notes

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