Ammonium Chloride → HCID 22050881, compound

HRID 1866966Notes

Reaction equation

HRID 1866966 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:6](=[O:18])[C:5]=1[Br:19])=[N+]=[N-].[NH4+].[Cl-:21]>C(OCC)(=O)C.O.[Fe]>[ClH:21].[NH2:1][C:4]1[CH:9]=[CH:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:6](=[O:18])[C:5]=1[Br:19]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 22050870HCID 22050870, compound

Product 1

HCID 22050881HCID 22050881, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-azido-3-bromo-1-(3-fluorobenzyl)pyridin-2(1H)-one (from step 2) (4.00 g, 12.38 mmol) was suspended in ethyl acetate (300 mL) and Fe (2.07 g, 37.14 mmol) was added. A stock solution of NH4Cl in H2O (300 mL, 0.2 M) was added and the reaction mixture was stirred at room temperature for 36 hours. The reaction was filtered through a pad of Celite® and concentrated. The resulting solid was dissolved in ethyl acetate (150 mL) and washed with water (3×50 mL), brine (50 mL), dried over MgSO4, and concentrated. 1H NMR (400 MHz, CD3OD) δ 7.38 7.29 (m, 2H), 7.05 (d, J=7.79 Hz, 1H), 6.99 (d, J=8.99 Hz, 2H), 6.03 (d, J=7.39 Hz 1H), 5.09 (s, 2H). ES-HRMS m/z 297.0023 (M+H C20H17BrF2N2O2 requires 297.0033).

Workup

  1. filtrationThe reaction was filtered through a pad of Celite®
  2. concentrationconcentrated
  3. dissolutionThe resulting solid was dissolved in ethyl acetate (150 mL)
  4. washwashed with water (3×50 mL), brine (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c1018248dfe84503bc9fc2bfd8529fdf
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

Loading…