2-Amino-5-bromopyridine → HCID 53812896, compound

HRID 379272Notes

Reaction equation

HRID 379272 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)[CH3:2].[NH2:24][C:25]1[CH:30]=[CH:29][C:28](Br)=[CH:27][N:26]=1.CC([O-])=O.[K+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:3][C:4](=[O:23])[CH:5]=[C:6]([C:28]1[CH:27]=[N:26][C:25]([NH2:24])=[CH:30][CH:29]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)[CH3:2]

Participants

6

Reactant 3

HCID 706222-Amino-5-bromopyridineHCID 517044Potassium AcetateHCID 53827885HCID 53827885, compound

Product 1

HCID 53812896HCID 53812896, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 28-4 (0.3 g, 1.0 mmol), 2-amino-5-bromopyridine (0.3 g, 1.9 mmol), KOAc (0.3 g, 2.4 mmol) and Pd(OAc)2 (0.02 g, 0.1 mmol) in 6 mL DMF was purged with argon for 5 min and then heated at 90° C. for 7 hr and 115° C. for 48 hr. It was cooled, treated with 50 mL water and extracted with EtOAc (×3). The combined organic layers were washed with brine and dried over Na2SO4. After solvent removal, the residue was purified using silica gel flash chromatography (100% EtOAc to EtOAc/MeOH 10:1) to afford the desired product 28-5 as an oil.

Workup

  1. customwas purged with argon for 5 min
  2. temperatureIt was cooled
  3. additiontreated with 50 mL water
  4. extractionextracted with EtOAc (×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter solvent removal
  8. customthe residue was purified

Sources & evidence

ORD record
ord-575aaf2d953b4ff6b9a993d5dcb1f72e
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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