4-Cyanophenylboronic acid → 4-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)benzonitrile

HRID 410159Notes

Reaction equation

HRID 410159 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24](Br)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].[C:26]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)#[N:27].O.C(=O)([O-])[O-].[Na+].[Na+]>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:31]3[CH:32]=[CH:33][C:28]([C:26]#[N:27])=[CH:29][CH:30]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

6

Reactant 3

HCID 27343264-Cyanophenylboronic acidHCID 2735133Sodium Carbonate MonohydrateHCID 59326957(1H-benzo[d]imidazol-2-yl)(4-(3-bromopyridin-2-yloxy)phenyl)methanone

Product 1

HCID 462160654-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A glass microwave reaction vessel was charged with (1H-benzo[d]imidazol-2-yl)(4-(3-bromopyridin-2-yloxy)phenyl)methanone (0.1427 g, 0.36 mmol), 4-cyanophenylboronic acid (0.0760 g, 0.43 mmol), trans-dichlorobis(triphenyl-phosphine)palladium(ii) (0.0314 g, 0.029 mmol), and sodium carbonate monohydrate (0.13 mL, 1.8 mmol) in 1,2-dimethoxymethane (3 mL) and water (1 mL). The reaction mixture was stirred and heated in a Biotage™ Initiator™ microwave reactor at 135° C. for 10 min. The solvent was evaporated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage™ pre-packed silica gel column (25M), eluting with a gradient of 10% to 80% ethyl acetate in hexane, to provide 4-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)benzonitrile. MS (ESI, pos. ion) m/z: 417.5 (M+1). IC50 (uM) +++++.

Workup

  1. customA glass microwave reaction vessel
  2. customThe solvent was evaporated
  3. customchromatographed through a Biotage™ pre-packed silica gel column (25M)
  4. washeluting with a gradient of 10% to 80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-83c94563c9ca4fa88bb5d5b99240cb18
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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