2-Pyridinecarboxamide → 4-(6-Bromopyridin-3-yl)-2-(pyridin-2-yl)oxazole

HRID 1187433Notes

Reaction equation

HRID 1187433 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([Br:11])=[CH:9][CH:10]=1)=O.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([NH2:20])=[O:19].C([O-])(O)=O.[Na+]>CCOC(C)=O>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:20]=[C:18]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=3)[O:19][CH:2]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 150702-PyridinecarboxamideHCID 516892Sodium BicarbonateHCID 108502672-bromo-1-(6-bromopyridin-3-yl)ethanone

Product 1

HCID 534020214-(6-Bromopyridin-3-yl)-2-(pyridin-2-yl)oxazoleYield 10%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-bromo-1-(6-bromopyridin-3-yl)ethanone from Step A (2.3 g, 8.25 mmol) and pyridine-2-carboxamide (1 g, 8.25 mmol) was melted at 85°. Heating was continued until the mixture reached 140° at which point the product solidified. Ice, EtOAc and sat aq NaHCO3 were added. The aqueous layer was then back extracted with EtOAc/THF (3:1). Pooled organics were dried over MgSO4, filtered, concentrated, and purified on silica gel to afford 250 mg (10% yield) of 2-bromo-5-(2-pyridin-2-yl-1,3-oxazole-4-yl)pyridine. LC/MS: m/e 302.0 (M+H).

Workup

  1. temperatureHeating
  2. customreached 140° at which point
  3. additionwere added
  4. extractionThe aqueous layer was then back extracted with EtOAc/THF (3:1)
  5. dry with materialPooled organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on silica gel

Sources & evidence

ORD record
ord-a530822333cf46f7b0623500ec3cd92f
Source dataset
uspto-grants-2014_03
Patent number
US08673941B2

Reaction notes

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