2-Amino-5-bromopyridine → HCID 57413704, compound

HRID 333924Notes

Reaction equation

HRID 333924 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:9][C:10]1[O:14][C:13]([CH2:15][CH2:16][C:17](Cl)=[O:18])=[CH:12][CH:11]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:17](=[O:18])[CH2:16][CH2:15][C:13]2[O:14][C:10]([CH3:9])=[CH:11][CH:12]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 10910039HCID 10910039, compound

Product 1

HCID 57413704HCID 57413704, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5-bromopyridin-2-amine (123a, 600 mg, 3.47 mmol) in pyridine (10 ml) was added 3-(5-Methyl-furan-2-yl)-propionyl chloride (718.3 mg, 4.16 mmol) and stirred at room temperature for 16 hours. The reaction mixture was then quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give N-(5-Bromo-pyridin-2-yl)-3-(5-methyl-furan-2-yl)-propionamide (123): 1H NMR (500 MHz, DMSO) δ: 10.68 (s, 1H), 10.68 (s, 1H),8.42 (d, 1H), 8.07 (m, 1H), 5.94 (s, 1H), 5.92 (s, 1H), 2.85 (t, 2H), 2.70 (t, 2H), 2.19 (s, 3H). ESI-MS: 310.2 (M+H)+.

Workup

  1. customThe reaction mixture was then quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4(s)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e2b32cd4e7764c5e825448b2073f0316
Source dataset
uspto-grants-2014_11
Patent number
US08883793B2

Reaction notes

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