3-Pyridinylboronic acid → HCID 57586462, compound

HRID 420353Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:37])[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](Br)[CH:25]=[C:24](Br)[CH:23]=2)[C:10]=1[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:2].[N:38]1[CH:43]=[CH:42][CH:41]=[C:40](B(O)O)[CH:39]=1>>[CH2:1]([O:3][C:4](=[O:37])[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:40]3[CH:39]=[N:38][CH:43]=[CH:42][CH:41]=3)[CH:25]=[C:24]([C:40]3[CH:39]=[N:38][CH:43]=[CH:42][CH:41]=3)[CH:23]=2)[C:10]=1[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:2]

Participants

Reactant 2

HCID 27343783-Pyridinylboronic acid

HCID 57586569HCID 57586569, compound

Product 1

HCID 57586462HCID 57586462, compoundYield 62.2%

Procedure

A similar procedure as described in Example 1, step 2 was used, starting from 4-{3-[6-(3,5-dibromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (250 mg, 0.39 mmol) and pyridin-3-ylboronic acid (201 mg, 1.55 mmol) to give 4-{3-[6-(3,5-di-pyridin-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (155 mg, 62%) as a colorless oil: ES(+)-HRMS m/e calculated for C39H46N2O6 (M+H)+ 639.3429, found 639.3416.

Sources & evidence

ORD record: ord-f12c428ecb0243878ff3ae45282e90e7
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093385B2

Reaction notes

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