2-Fluoropyridine-4-boronic acid → HCID 57586564, compound

HRID 420351Notes

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].[F:38][C:39]1[CH:44]=[C:43](B(O)O)[CH:42]=[CH:41][N:40]=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:43]3[CH:42]=[CH:41][N:40]=[C:39]([F:38])[CH:44]=3)[CH:25]=[C:24]([C:43]3[CH:42]=[CH:41][N:40]=[C:39]([F:38])[CH:44]=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 27833962-Fluoropyridine-4-boronic acid

HCID 57586569HCID 57586569, compound

Product 1

HCID 57586564HCID 57586564, compoundYield 67%

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 (321 mg, 0.5 mmol) and 2-fluoro-pyridin-4-ylboronic acid (422 mg, 3.0 mmol) to isolate 4-[3-{6-[3,5-bis-(2-fluoro-pyridin-4-yl)-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (225 mg, 67%) as a colorless oil: ES(+)-HRMS m/e calculated for C39H44F2N2O6 (M+H)+ 675.3240, found 675.3238.

Sources & evidence

ORD record: ord-2a1743656eb348b3abd4a142ee2ae7e2
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093385B2

Reaction notes

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