Phenylboronic Acid → HCID 59654690, compound

HRID 1444241Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](Br)[N:16]=2)=[O:14])[CH:7]=1)[CH3:2].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:16]=2)=[O:14])[CH:7]=1)[CH3:2]

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 59654644HCID 59654644, compound

Product 1

HCID 59654690HCID 59654690, compound

Conditions

Temperature: 80 °C

Procedure

{3-[(6-Bromo-pyridine-2-carbonyl)-amino]-phenyl}-acetic acid ethyl ester (77) (198 mg, 0.54 mmol) was coupled to phenylboronic acid using Method E, except that the reaction mixture was heated at 80° C. for 25 min. The crude product was purified by column chromatography using 20% EtOAc in heptane to give the title compound.

Workup

customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-aa9ff05133144c979c8d3f4b808faa87
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662839B2

Reaction notes

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