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

HRID 914696Notes

Reaction equation

HRID 914696 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-54c4db8cf9fc4090b35a91c37b7ef82b
Source dataset
uspto-grants-2007_09
Patent number
US07265104B2

Reaction notes

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