Water → 2-Acetamido-5-bromopyridine

HRID 383260Notes

Reaction equation

HRID 383260 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.N1C=CC=CC=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].O>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:15](=[O:17])[CH3:16])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 2930972-Acetamido-5-bromopyridineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-bromopyridine (0.50 g, 2.9 mmol) in THF (10 mL) was added pyridine (343 mg, 4.3 mmol) and acetic anhydride (295 mg, 2.9 mmol) at room temperature and stirred overnight. To the mixture water (30 mL) was added, extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, concentrated to give the title compound (0.58 g, 92%) as a white solid LCMS: 215 [M+2]+; 1HNMR (400 MHz, DMSO-d6) δ 2.09 (s, 3H), 7.97 (dd, J=8.8, 2.4 Hz, 1H), 8.06 (d, J=8.8 Hz, 1H), 8.41 (d, J=1.2 Hz, 1H), 10.64 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. washThe combined organic layers were washed with saturated aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5820e6b389f744bfb7cce4f9c7059db1
Source dataset
uspto-grants-2013_02
Patent number
US08367663B2

Reaction notes

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