Methanol → HCID 86680798, compound

HRID 2402375Notes

Reaction equation

HRID 2402375 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].CO>CN(C1C=CN=CC=1)C.C1COCC1>[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 4

HCID 887MethanolHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 140910412,6-Dibromopyridin-4-amine

Product 1

HCID 86680798HCID 86680798, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-dibromopyridin-4-amine (1.0 g, 3.97 mmol), DMAP (0.048 g, 0.397 mmol), and pyridine (0.482 mL, 5.95 mmol) in THF (7.94 mL) at rt was slowly added acetic anhydride (0.412 mL, 4.37 mmol), and the mixture was stirred at rt for 16 h, after which time the reaction was heated to 65° C. for a period of 5 days. After cooling to rt, MeOH (5 mL) was added and the reaction was concentrated under reduced pressure. The product was purified by silica gel chromatography using a gradient solvent system of 0-100% EtOAc/Hexanes. The product-containing fractions were collected and concentrated under reduced pressure to give N-(2,6-dibromopyridin-4-yl)acetamide (1.10 g, 94%) as a yellow solid. MS ESI calcd for C7H6Br2N2O [M+H]+ 293, found 293.

Workup

  1. customat rt
  2. temperatureafter which time the reaction was heated to 65° C. for a period of 5 days
  3. temperatureAfter cooling to rt
  4. concentrationthe reaction was concentrated under reduced pressure
  5. customThe product was purified by silica gel chromatography
  6. customThe product-containing fractions were collected
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44c43a32fe324c61972e5d25a5872e10
Source dataset
uspto-grants-2014_08
Patent number
US08796310B2

Reaction notes

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