2-Amino-5-bromopyridine → HCID 12269134, compound

HRID 751266Notes

Reaction equation

HRID 751266 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6](=O)[CH2:7]Br)[CH3:2].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]=1>C(#N)C>[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6]1[N:11]=[C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]2[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 575284Ethyl 4-bromo-3-oxobutanoate

Product 1

HCID 12269134HCID 12269134, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add 4-bromo-3-oxo-butyric acid ethyl ester (12.08 g, 57.8 mmol) to a solution of 2-amino-5-bromo pyridine (5.0 g, 28.9 mmol) in acetonitrile (80 mL). Reflux for 4 days and concentrate to dryness. Purify by flash chromatography using appropriate ethyl acetate/methanol mixtures to give the subtitled compound (5.75 g, 70%) as a brown oil. TOF MS ES+ exact mass calculated for C, HI BrN2O2 (p+1): m/z=283.0082 Found: 283.0084. 1H NMR (400 MHz, DMSO-d6) δ 8.68 (m, 1H), 7.82 (s, 1H), 7.45 (d, J=10 Hz, 1H), 7.30 (dd, J=10, 2.0 Hz, 1H), 4.08 (q, J=7.0 Hz, 2H), 3.77 (s, 2H), 1.18 (t, J=7.0 Hz, 3H).

Workup

  1. temperatureReflux for 4 days
  2. concentrationconcentrate to dryness
  3. customPurify by flash chromatography

Sources & evidence

ORD record
ord-5e3f2c19640f48348f39ef3e3b32c1aa
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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