Sodium hydride → HCID 10289584, compound

HRID 1985142Notes

Reaction equation

HRID 1985142 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C([O:12][C:13](=[O:41])[C:14]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[F:40])([CH3:32])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH:25]2[CH2:29][NH:28][C:27](=[O:30])[N:26]2[CH3:31])=[CH:18][CH:17]=1)C.[H-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:28]2[CH2:29][CH:25]([CH2:24][CH2:23][O:22][C:19]3[CH:18]=[CH:17][C:16]([CH2:15][C:14]([O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[F:40])([CH3:32])[C:13]([OH:41])=[O:12])=[CH:21][CH:20]=3)[N:26]([CH3:31])[C:27]2=[O:30])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 68867329HCID 68867329, compound

Product 1

HCID 10289584HCID 10289584, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Chlorobenzyl bromide (0.035 g, 0.172 mmol) 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 (0.051 g, 0.115 mmol) and sodium hydride (0.011 g, 0.287 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 purified by LCMS to provide the title compound. 1H NMR (400 MHz, CDCl3): δ 7.31-7.22 (m, 5H), 7.15-7.01 (m, 5H), 6.74 (d, 2H, J=7.8 Hz), 4.34 (d, 2H, J=14.3 Hz), 3.96 (s, 2H), 3.73-3.71 (m, 1H), 3.46-3.40 (m, 1H), 3.28, 3.16 (ABq, 2H, J=14.3 Hz), 3.08-3.06 (m, 1H), 2.85 (s, 3H), 2.23-2.20 (m, 1H), 1.91-1.89 (m, 1H), 1.41 (s, 3H). MS [ES+] m/z exact mass calcd for C29H31N2O5FCl 541.1906, found 541.1909.

Workup

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

Sources & evidence

ORD record
ord-a76e719b0dc04e30a6e9cddee9cc0c5a
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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