Pyridine → HCID 22093472, compound

HRID 457959Notes

Reaction equation

HRID 457959 reaction equation
[CH2:1]([O:4][C:5](=[O:27])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=1[C:15](=[O:26])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1[F:25])[CH:2]=[CH2:3].N1C=CC=CC=1.[C:34](OC(=O)C)(=[O:36])[CH3:35].C(OCC)(=O)C>O1CCCC1>[CH2:1]([O:4][C:5](=[O:27])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:34](=[O:36])[CH3:35])=[CH:10][C:9]=1[C:15](=[O:26])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1[F:25])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 22093473[4-Amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester

Product 1

HCID 22093472HCID 22093472, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [4-amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester (0.13 g, 0.30 mmol) was dissolved in tetrahydrofuran (2 mL, 0.2 M) along with pyridine (0.05 mL, 0.05 g, 0.61 mmol). This mixture was cooled to 0° C. before treatment with acetic anhydride (0.10 mL, 0.098 g, 0.95 mmol). After stirring at room temperature for 24 h, the reaction mixture was diluted ethyl acetate and sucessively washed with 2 N HCl, saturated aq NaHCO3 and saturated aq NaCl. The organic layer was dried over Na2SO4, filtered and concentrated to give [4-acetylamino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester (0.125 g, 87%): 1H NMR (DMSO-d6, 300 MHz) δ 89.95 (br s, 1 H), 8.94 (br t, J=5.7 Hz, 1 H), 7.98 (d, J=2.7 Hz, 1 H), 7.74 (dd, J1=9.0 Hz, J2=3.0 Hz, 1 H), 7.42–7.24 (m, 2 H), 7.22–7.02 (m, 2 H), 5.88 (m, 1 H), 5.30 (dd, J1=17.1 Hz, J2=1.8 Hz, 1 H), 5.21 (dd, J1=9.0 Hz, J2=1.8 hz, 1 H), 4.97 (s, 2 H), 4.64 (br d, J=5.4 Hz, 2 H), 4.55 (br d, J=6.0 Hz, 2 H), 2.00 (s, 3H).

Workup

  1. washsucessively washed with 2 N HCl, saturated aq NaHCO3 and saturated aq NaCl
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c5dea1a99aeb4d0d94abd9cfbd246843
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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