(Pyridin-4-yl)boronic acid → HCID 25191879, compound

HRID 420382Notes

Reaction equation

[C:1]([CH2:4][CH2:5][C:6]1[C:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:27]=[C:28]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=3)[CH:29]=[C:30](I)[CH:31]=2)=[CH:17][CH:16]=[CH:15][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])([OH:3])=[O:2].[N:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1>>[C:1]([CH2:4][CH2:5][C:6]1[C:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:27]=[C:28]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=3)[CH:29]=[C:30]([C:43]3[CH:44]=[CH:45][N:40]=[CH:41][CH:42]=3)[CH:31]=2)=[CH:17][CH:16]=[CH:15][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])([OH:3])=[O:2]

Participants

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acid

HCID 57586519HCID 57586519, compound

Product 1

HCID 25191879HCID 25191879, compoundYield 26%

Procedure

A similar procedure as described in Example 5, step 2 was used, starting from 4-{2-(2-carboxy-ethyl)-3-[6-(3′-fluoro-5-iodo-bi phenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid (116 mg, 0.18 mmol) and pyridin-4-ylboronic acid (66 mg, 0.54 mmol) to obtain 4-{2-(2-carboxy-ethyl)-3-[6-(3′-fluoro-5-pyridin-4-yl-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid (28 mg, 26%) as an amorphous white solid: ES(+)-HRMS m/e calculated for C36H38FNO6 (M+H)+ 600.2756, found 600.2754.

Sources & evidence

ORD record: ord-0218436336d54db1be2ed1c2eb2d9e0b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093385B2

Reaction notes

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