Cesium carbonate → HCID 59327181, compound

HRID 1880170Notes

Reaction equation

HRID 1880170 reaction equation
F[C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[C:18]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O.CCOC(C)=O>[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:2]2[C:7]([I:8])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:22][CH:21]=1)=[O:19]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 70095012-Fluoro-3-iodopyridineHCID 59326874(1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone

Product 1

HCID 59327181HCID 59327181, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
115 °C

Procedure

A solution of 2-fluoro-3-iodopyridine (3.052 g, 13.69 mmol), (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (4.89 g, 20.53 mmol) and cesium carbonate (7.58 g, 23.27 mmol) in N-Methyl-2-pyrrolidinone (20 mL) was degassed and heated to 115° C. After 64 h, the reaction was cooled to 23° C., diluted with EtOAc (250 mL) and washed with water (100 mL) and brine (75 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 0.5-1.5% methanol/dichloromethane), affording the product as a yellow solid. MS (ESI, pos. ion) m/z: 404.1 (M+1).

Workup

  1. temperaturethe reaction was cooled to 23° C.
  2. washwashed with water (100 mL) and brine (75 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography (eluant: 0.5-1.5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-9429efdf1c474276bcb6855980cb3365
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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