2-Naphthol → 4-(3-Methyl-3H-imidazole-4-carbonyl)-2-(naphthalen-2-yloxy)-benzonitrile

HRID 379065Notes

Reaction equation

HRID 379065 reaction equation
F[C:2]1[CH:9]=[C:8]([CH:10]([OH:17])[C:11]2[N:12]([CH3:16])[CH:13]=[N:14][CH:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[OH:28].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH3:16][N:12]1[C:11]([C:10]([C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([O:28][C:19]3[CH:20]=[CH:21][C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:18]=3)[CH:9]=2)=[O:17])=[CH:15][N:14]=[CH:13]1

Participants

6

Reactant 3

HCID 86632-NaphtholHCID 10796Cesium carbonateHCID 185332012-Fluoro-4-(hydroxy(1-methyl-1h-imidazol-5-yl)methyl)benzonitrile

Product 1

HCID 216969884-(3-Methyl-3H-imidazole-4-carbonyl)-2-(naphthalen-2-yloxy)-benzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

2-Fluoro-4-[hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile (as described in Example 22, Step E) (0.172 g, 0.743 mmol), 2-naphthol (0.107 g, 0.743 mmol) and Cs2CO3 (0.727 g, 2.23 mmol) were dissolved in anhydrous DMF (5 mL) and heated at 60° C. under Ar for 2 days. The reaction was diluted with EtOAc, washed with satd. NaHCO3 solution, water, and brine. The organic layer was dried (MgSO4), concentrated and purified using SiO2 chromatography (1-2% MeOH/CH2Cl2) to give the title compound.

Workup

  1. washwashed with satd
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-0019dd6f329e49b0ae5a9b71a60da490
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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