2-Cyclopenten-1-one → 3-(2-(4-(1H-Benzo[D]imidazole-2-carbonyl)phenoxy)pyridin-3-YL)cyclopent-2-enone

HRID 410296Notes

Reaction equation

HRID 410296 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]1(=[O:31])[CH2:30][CH2:29][CH:28]=[CH:27]1>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[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:28]3[CH2:29][CH2:30][C:26](=[O:31])[CH:27]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

5

Reactant 2

HCID 135882-Cyclopenten-1-oneHCID 59326957(1H-benzo[d]imidazol-2-yl)(4-(3-bromopyridin-2-yloxy)phenyl)methanone

Product 1

HCID 462148723-(2-(4-(1H-Benzo[D]imidazole-2-carbonyl)phenoxy)pyridin-3-YL)cyclopent-2-enone

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

A suspension of (1H-benzo[d]imidazol-2-yl)(4-(3-bromopyridin-2-yloxy)phenyl)methanone (500 mg, 1.268 mmol), 2-cyclopenten-1-one (0.410 mL, 5.07 mmol), 105° C. and bis(tri-tert-butylphosphine)palladium (0) (64.8 mg, 0.127 mmol) in Dioxane (4 mL) was capped, degassed and backfilled with argon. The reaction was heated at 105° C. After 6 h, the reaction was cooled to 23° C., concentrated in vacuo and purified by silica gel chromatography (eluant: 40-100% EtOAc/hexane), affording the product as a yellow solid. MS (ESI, pos. ion) m/z: 396.1 (M+1). IC50 (uM) +++++.

Workup

  1. customwas capped
  2. customdegassed
  3. temperaturethe reaction was cooled to 23° C.
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography (eluant: 40-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-ec75562d7dc1418992e9f992e958c4f9
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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