(Pyridin-4-yl)boronic acid → HCID 86628185, compound

HRID 420388Notes

Reaction equation

C(OC(=O)CCC[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](I)[CH:25]=[C:24]([C:29]3[CH:37]=[CH:36][C:32]4[O:33][CH2:34][O:35][C:31]=4[CH:30]=3)[CH:23]=2)[C:10]=1[CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])C.[N:46]1[CH:51]=[CH:50][C:49](B(O)O)=[CH:48][CH:47]=1>>[CH2:43]([O:42][C:40](=[O:41])[CH:39]([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:49]3[CH:50]=[CH:51][N:46]=[CH:47][CH:48]=3)[CH:25]=[C:24]([C:29]3[CH:37]=[CH:36][C:32]4[O:33][CH2:34][O:35][C:31]=4[CH:30]=3)[CH:23]=2)[C:10]=1[CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:38][CH3:10])[CH3:44]

Participants

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acid

HCID 57586500HCID 57586500, compound

Product 1

HCID 86628185HCID 86628185, compoundYield 124.7%

Procedure

A similar procedure as described in Example 12, step 8 was used, starting from 4-{3-[6-(3-benzo[1,3]dioxol-5-yl-5-iodo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (87 mg, 0.12 mmol) and pyridin-4-ylboronic acid (45 mg, 0.36 mmol) to afford 4-{3-[6-(3-benzo[1,3]dioxol-5-yl-5-pyridin-4-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy-butyric acid ethyl ester (51 mg, 63%) as a light yellow oil: ES(+)-HRMS m/e calculated for C41H47NO8 (M+H)+ 682.3375, found 682.3369.

Sources & evidence

ORD record: ord-1678a4a69b084892a0d564da03c301d6
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093385B2

Reaction notes

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