Pyridine → HCID 86680798, compound

HRID 595175Notes

Reaction equation

HRID 595175 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Br:9])[N:3]=1.N1C=CC=CC=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>CN(C1C=CN=CC=1)C.C1COCC1.CO>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:16](=[O:18])[CH3:17])[CH:5]=[C:4]([Br:9])[N:3]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 140910412,6-Dibromopyridin-4-amine

Product 1

HCID 86680798HCID 86680798, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,6-Dibromopyridin-4-amine, DMAP (0.048 g, 0.397 mmol) and pyridine (0.48 ml, 5.95 mmol) were taken-up in THF (7.9 ml) under argon. Acetic anhydride (0.41 ml, 4.37 mmol) was slowly added and the mixture was stirred overnight at room temperature. The reaction was then heated to 65° C. for 5 days and cooled to room temperature, diluted with methanol, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-100% EtOAc/hexanes) to afford N-(2,6-dibromopyridin-4-yl)acetamide as a light yellow solid. MS ESI calc'd. for C7H6Br2N2O [M+H]+ 294. found 294.

Workup

  1. temperatureThe reaction was then heated to 65° C. for 5 days
  2. temperaturecooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5441c20b37b64513a114efbd267ff5b5
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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