(Pyrimidin-5-yl)boronic acid → HCID 68750403, compound

HRID 420390Notes

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]=[C:50](B(O)O)[CH:49]=[N: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:51]3[CH:50]=[CH:49][N:48]=[CH:47][N:46]=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 2795193(Pyrimidin-5-yl)boronic acid

HCID 57586500HCID 57586500, compound

Product 1

HCID 68750403HCID 68750403, compoundYield 151.3%

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 (47 mg, 0.06 mmol) and pyrimidin-5-ylboronic acid (32 mg, 0.26 mmol) to afford 4-{3-[6-(3-benzo[1,3]dioxol-5-yl-5-pyrimidin-4-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy-butyric acid ethyl ester (31 mg, 71%) as a light yellow oil: ES(+)-HRMS m/e calculated for C40H46N2O8 (M+H)+ 683.3327, found 683.3327.

Sources & evidence

ORD record: ord-8e49783788cb492d96b104582742d265
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093385B2

Reaction notes

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