HCID 18468176, compound → HCID 12968791, compound

HRID 457957Notes

Reaction equation

HRID 457957 reaction equation
[Br:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][C:11]=2[O:12][CH2:13][C:14]([OH:16])=[O:15])=[O:9])=[C:4]([F:26])[CH:3]=1.[H][H]>C(O)C.[Pd]>[NH2:21][C:19]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[C:10]([C:8](=[O:9])[NH:7][CH2:6][C:5]2[CH:24]=[CH:25][C:2]([Br:1])=[CH:3][C:4]=2[F:26])[CH:20]=1

Participants

5

Reactant 2

HCID 18468176HCID 18468176, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12968791HCID 12968791, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[2-(4-Bromo-2-fluoro-benzylcarbamoyl)-4-nitro-phenoxy]-acetic acid (1.10 g, 2.76 mmol) was dissolved in ethyl alcohol (40 mL, 0.1 M), treated with 10% Pd on carbon (Degussa, 0.10 g) and placed under a balloon of hydrogen for 12 h. The reaction was filtered through Celite and concentrated to give a crude solid which was recrystallized from heptane and ethyl acetate to give [4-amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid (0.79 g, 66%): mp 204° C. (dec.); Rf 0.10 (10% methanol in dichloromethane); 1H NMR (DMSO-d6, 300 MHz) δ 9.16 (br t, J=6.3 Hz, 1 H), 7.85 (d, J=2.7 Hz, 1 H), 7.46–7.11 (m, 5 H), 4.91 (s, 2 H), 4.57 (br d, J=3.6 Hz, 2 H). ESI-LC/MS m/z calcd for C16H14BrFN2O4: 396.0 found 395.0 (M−1)−. Anal. calcd for C16H14BrFN2O4: C, 48.38; H, 3.55; N, 7.05. Found C, 48.05; H, 4.02; N, 6.94.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. concentrationconcentrated
  3. customto give a crude solid which
  4. customwas recrystallized from heptane and ethyl acetate

Sources & evidence

ORD record
ord-767c5e6be7bc46cbab58b7a20901a4df
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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