5-Indolylboronic acid → HCID 46888200, compound

HRID 420383Notes

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].[NH:40]1[C:48]2[C:43](=[CH:44][C:45](B(O)O)=[CH:46][CH:47]=2)[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:45]3[CH:44]=[C:43]4[C:48](=[CH:47][CH:46]=3)[NH:40][CH:41]=[CH:42]4)[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 27343615-Indolylboronic acid

HCID 57586519HCID 57586519, compound

Product 1

HCID 46888200HCID 46888200, compoundYield 31%

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 (116 mg, 0.18 mmol) and 1H-indol-5-ylboronic acid (66 mg, 0.54 mmol) to obtain 4-(2-(2-carboxy-ethyl)-3-{6-[3′fluoro-5-(1H-indol-5-yl)-biphenyl-3-yloxy]-hexyl}-phenoxy)-butyric acid (35 mg, 31%) as an amorphous light yellow solid: ES(+)-HRMS m/e calculated for C39H40FNO6 (M+Na)+ 660.2732, found 660.2735.

Sources & evidence

ORD record: ord-1dd86681aee24cf293367cc9b7a4cd8c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093385B2

Reaction notes

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