2-Amino-4-bromopyridine → HCID 58574614, compound

HRID 1619393Notes

Reaction equation

HRID 1619393 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:7][CH2:6][CH:5]([C:8]([O:10]C)=O)[C:4](=O)[CH2:3]1.[Br:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=1>ClCCCl>[Br:14][C:15]1[CH:20]=[CH:19][N:18]2[C:17](=[N:21][C:4]3[CH2:3][C:2]([CH3:1])([CH3:13])[CH2:7][CH2:6][C:5]=3[C:8]2=[O:10])[CH:16]=1

Participants

4

Reactant 2

HCID 6932822-Amino-4-bromopyridineHCID 5314361METHYL 4,4-DIMETHYL-2-OXOCYCLOHEXANECARBOXYLATE

Product 1

HCID 58574614HCID 58574614, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of methyl 4,4-dimethyl-2-oxocyclohexanecarboxylate (0.5 g, 2.7 mmol, 1 eq), 4-bromopyridin-2-amine (0.51 g, 2.97 mmol, 1.1 eq) and PPA in 1,2-dichloroethane was stirred at 80° C. for 4 hours. After it was cooled to rt, the reaction mixture was quenched with saturated Na2CO3 and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product.

Workup

  1. customthe reaction mixture was quenched with saturated Na2CO3
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fa471324beb44130a7ba48fa5acba095
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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