3-Fluorophenylboronic acid → 5-(3-Fluoro-phenyl)-furan-2-carboxylic acid (3-cyanomethyl-phenyl)-amide

HRID 1444290Notes

Reaction equation

HRID 1444290 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[O:14][C:15](Br)=[CH:16][CH:17]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1)#[N:2].[F:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1>>[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[O:14][C:15]([C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([F:19])[CH:25]=3)=[CH:16][CH:17]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1)#[N:2]

Participants

3

Reactant 2

HCID 27339863-Fluorophenylboronic acidHCID 596548595-Bromo-furan-2-carboxylic acid (3-cyanomethyl-phenyl)-amide

Product 1

HCID 596547745-(3-Fluoro-phenyl)-furan-2-carboxylic acid (3-cyanomethyl-phenyl)-amide

Procedure

The furyl bromide (83) (135 mg, 0.44 mmol) was coupled to 3-fluoro-phenylboronic acid (68 mg, 0.49 mmol) using Method E. The crude residue was purified by column chromatography eluting with 20% EtOAc in heptane to give the title compound.

Workup

  1. customThe crude residue was purified by column chromatography
  2. washeluting with 20% EtOAc in heptane

Sources & evidence

ORD record
ord-17e6d2c2024d48109da017301f11d32e
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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