Sodium hydride → HCID 66920434, compound

HRID 1510061Notes

Reaction equation

HRID 1510061 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.[H-].[Na+].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:28]=2Cl)=[O:26])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>CN1C(=O)CCC1>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH2:21][N:22]([C:25]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:28]=2[O:8][C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[CH3:9])=[O:26])[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27746165-Fluoro-2-methylphenolHCID 45257316HCID 45257316, compound

Product 1

HCID 66920434HCID 66920434, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 5-fluoro-2-methylphenol (43.0 mg, 341 μmol) in NMP (1.5 ml) was added sodium hydride (15.0 mg, 375 μmol; 60% dispersion in mineral oil), and the suspension was stirred at room temperature under an argon atmosphere for 20 min. After addition of 50.0 mg (114 μmol) of the compound of step 1, the reaction mixture was stirred for 2 h at 150° C. in a microwave reactor. The mixture was filtered and purified by preparative HPLC. The eluate was lyophilized overnight to give 23 mg of the title compound.

Workup

  1. stirringthe reaction mixture was stirred for 2 h at 150° C. in a microwave reactor
  2. filtrationThe mixture was filtered
  3. custompurified by preparative HPLC
  4. waitThe eluate was lyophilized overnight

Sources & evidence

ORD record
ord-e89affb05f7e4ff7a878970d5cf0928d
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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