Sodium hydride → HCID 68867419, compound

HRID 1985145Notes

Reaction equation

HRID 1985145 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br.[CH2:13]([O:15][C:16](=[O:44])[C:17]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[F:43])([CH3:35])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH:28]2[CH2:32][NH:31][C:30](=[O:33])[N:29]2[CH3:34])=[CH:21][CH:20]=1)[CH3:14].[H-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH2:13]([O:15][C:16](=[O:44])[C:17]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[F:43])([CH3:35])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH:28]2[CH2:32][N:31]([CH2:6][C:5]3[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:12])([F:11])[F:1])[CH:4]=3)[C:30](=[O:33])[N:29]2[CH3:34])=[CH:21][CH:20]=1)[CH3:14]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 68867329HCID 68867329, compound

Product 1

HCID 68867419HCID 68867419, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-Trifluoromethylbenzyl bromide (0.03 mL, 0.165 mmol, d=1.565) and tetrabutyl ammonium iodide (catalytic amount) are added to a 0° C. suspension of 2-(2-Fluoro-phenoxy)-2-methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester (0.049 g, 0.110 mmol) and sodium hydride (0.011 g, 0.276 mmol, 60% suspension on mineral oil), pre-stirred for 1 h at ambient temperature. The reaction mixture is stirred at ambient temperature for 18 h, diluted with ethyl acetate, and washed. The organic layer is dried, concentrated, and carried into the next step. MS [EI+] 603 (M+H)+.

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 18 h
  2. washwashed
  3. customThe organic layer is dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-725966bc793e45faa529c522824fbc79
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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