Water → N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-acetamide

HRID 1784837Notes

Reaction equation

HRID 1784837 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=[C:6]([Br:8])[CH:7]=1.C(N(C(C)C)CC)(C)C.[C:26](Cl)(=[O:28])[CH3:27].O>ClC(Cl)C>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:26](=[O:28])[CH3:27])[CH:3]=[C:4]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 50994432(3-Amino-5-bromo-phenyl)-pyridin-3-yl-methanone

Product 1

HCID 50994355N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-acetamide

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To 0.2 g of (3-amino-5-bromo-phenyl)-pyridin-3-yl-methanone in 10 mL of dichloroethane was added 0.126 mL of diisopropyl ethyl amine and 0.051 mL of acetyl chloride. The reaction mixture was stirred for 10 minutes then poured into water and extracted twice with CH2Cl2. The organic phase was dried over sodium sulfate, filtered and and concentrated to give 154 mg of N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-acetamide, which was used without further purification. 1H NMR (400 MHz, methanol-d4/CDCl3): δ 8.89 (d, J=2.0 Hz, 1H), 8.76 (dd, J=4.9, 1.6 Hz, 1H), 8.17 (dt, J=4.9, 2.7 Hz, 1H), 8.11 (t, J=1.8 Hz, 1H), 7.90 (t, J=1.6 Hz, 1H), 7.61-7.55 (m, 2H), 2.11 (s, 3H).

Workup

  1. extractionextracted twice with CH2Cl2
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2b15b8fa88a84ff08653dbd6ba33a023
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

Loading…