Bromoacetyl bromide → 2-bromo-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide

HRID 900118Notes

Reaction equation

HRID 900118 reaction equation
[CH:1]([NH:4][C:5]1[CH:6]=[N:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[Br:22][CH2:23][C:24](Br)=[O:25]>C(Cl)Cl.O>[Br:22][CH2:23][C:24]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5]1[CH:6]=[N:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)=[O:25]

Participants

6

Reactant 3

HCID 61147Bromoacetyl bromideHCID 81531DiisopropylethylamineHCID 28422728Isopropyl-(6-methoxy-pyridin-3-yl)-amine

Product 1

HCID 589579112-bromo-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamideYield 19.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of isopropyl-(6-methoxy-pyridin-3-yl)-amine (6.73 g, 41.0 mmol) in CH2Cl2 (130 mL) at 0° C. was added diisopropylethylamine (7.15 mL, 41.0 mmol) followed by bromoacetyl bromide (8.28 g, 41.0 mmol) in CH2Cl2 (60 mL) over 0.5 hours. The reaction was stirred at room temperature for 24 hours and was diluted with water. The organic solution was washed with brine (1×), dried (MgSO4), filtered and concentrated. The residue was purified by medium pressure chromatography eluting with a solvent gradient (1% MeOH in CH2Cl2 to 5% MeOH in CH2Cl2) to provide 2.27 g of 2-bromo-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide. 1H NMR (CD3OD) δ 8.08 (d, 1H), 7.62 (dd, 1H), 6.89 (d, 1H), 4.84 (m, 1H), 3.9 (s, 3H), 3.60 (s, 2H), 1.06 (m, 6H).

Workup

  1. washThe organic solution was washed with brine (1×)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by medium pressure chromatography
  6. washeluting with a solvent gradient (1% MeOH in CH2Cl2 to 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-72b401f350b24a4a96f7b470b4aec23a
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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