(2H-1,3-benzodioxol-5-yl)boronic acid → HCID 25192471, compound

HRID 420381Notes

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].[O:40]1[C:44]2[CH:45]=[CH:46][C:47](B(O)O)=[CH:48][C:43]=2[O:42][CH2:41]1>>[O:40]1[C:44]2[CH:45]=[CH:46][C:47]([C:30]3[CH:31]=[C:26]([O:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:18]4[C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])=[C:7]([CH:15]=[CH:16][CH:17]=4)[O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:27]=[C:28]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=4)[CH:29]=3)=[CH:48][C:43]=2[O:42][CH2:41]1

Participants

Reactant 2

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acid

HCID 57586519HCID 57586519, compound

Product 1

HCID 25192471HCID 25192471, compoundYield 62%

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-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid (1.2 g, 1.85 mmol) and benzo[1,3]dioxol-5-yl-boronic acid (614 mg, 3.7 mmol) to obtain 4-{3-[6-(5-benzo[1,3]dioxol-5-yl-3′-fluoro-biphenyl-3-yloxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy}-butyric acid (737 mg, 62%) as an amorphous white solid: ES(+)-HRMS m/e calculated for C38H39FO8 (M+Na)+ 665.2521, found 665.2520.

Sources & evidence

ORD record: ord-89463d5a938a44009bc310f48ba6329d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093385B2

Reaction notes

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