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Sodium hydride → HCID 10129032, compound

HRID 1985134
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Reaction equation

HRID 1985134 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.C([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)C.[H-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[F:43][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[O:36][C:17]([CH3:35])([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][CH:28]2[CH2:32][N:31]([CH2:7][C:6]3[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=3)[C:30](=[O:33])[N:29]2[CH3:34])=[CH:23][CH:24]=1)[C:16]([OH:44])=[O:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 68867329HCID 68867329, compound

Product 1

HCID 10129032HCID 10129032, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalyst
HCID 8857
Ethyl Acetate
Solvent

Procedure

4-Trifluoromethylbenzyl bromide (0.03 mL, 0.169 mmol, d=1.546) 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 (0.050 g, 0.112 mmol) and sodium hydride (0.011 g, 0.281 mmol, 60% suspension on mineral oil), and 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 with 1N HCl, water, and brine. The organic layer is dried, concentrated, and purified by LCMS. 1H NMR (400 MHz, CDCl3): δ 7.54 (d, 1H, J=7.8 Hz), 7.35 (d, 1H, J=7.8 Hz), 7.25-7-21 (m, 3H), 7.16 (d, 1H, J=7.8 Hz), 7.08-6.95 (m, 4H), 6.73 (d, 2H, J=7.8 Hz), 4.45, 4.37 (ABq, 2H, L=15.0 Hz), 3.95 (t, 2H, J=5.9 Hz), 3.68-3.60 (m, 1H), 3.38 (t, 1H, J=8.5 Hz), 3.29, 3.15 (ABq, 2H, J=13.7 Hz), 3.02-2.97 (m, 1H), 2.84 (s, 3H), 2.25-2.19 (m, 1H), 1.92-1.83 (m, 1H), 1.39 (s, 3H). MS [ES+] m/z exact mass calcd for C30H31N2O5F4 575.2169, found 575.2172.

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 18 h
  2. washwashed with 1N HCl, water, and brine
  3. customThe organic layer is dried
  4. concentrationconcentrated
  5. custompurified by LCMS

Sources & evidence

ORD record
ord-a38ddfe193e24b9daa3c6cbe803525fb
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07544812B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes