2-Cyclopentene-1-ol → HCID 46214875, compound

HRID 410306Notes

Reaction equation

HRID 410306 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](I)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].[CH:26]1([OH:31])[CH2:30][CH2:29][CH:28]=[CH:27]1.C([O-])(=O)C.[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)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]([CH:28]3[CH2:29][CH2:30][C:26](=[O:31])[CH2:27]3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

8

Reactant 3

HCID 2201642-Cyclopentene-1-olHCID 517044Potassium AcetateHCID 59327181HCID 59327181, compound

Product 1

HCID 46214875HCID 46214875, compound

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of (1H-benzo[d]imidazol-2-yl)(4-(3-iodopyridin-2-yloxy)phenyl)methanone (4.138 g, 9.38 mmol), cyclopent-2-enol (3.16 g, 37.5 mmol), tetrabutylammonium chloride (2.87 g, 10.32 mmol), potassium acetate (1.841 g, 18.76 mmol) and palladium (II) acetate (0.211 g, 0.938 mmol) in acetonitrile (30 mL) (argon bubbled through for 30 min) and water (3.00 mL) in a round bottom flask was capped with a septum, degassed, backfilled with argon and heated to 85° C. After 23 h, the reaction was cooled to 23° C., diluted with dichloromethane (200 mL) and washed with brine (2×150 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 35-50% EtOAc/hexane), affording the product as an off-white solid. MS (ESI, pos. ion) m/z: 398.1 (M+1). IC50 (uM) +++++.

Workup

  1. customwas capped with a septum
  2. customdegassed
  3. temperaturethe reaction was cooled to 23° C.
  4. additiondiluted with dichloromethane (200 mL)
  5. washwashed with brine (2×150 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. custompurified by silica gel chromatography (eluant: 35-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-ddb7fd0a036344e2ad3e8be3b15b593b
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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