2-Amino-4-bromopyridine → HCID 58574592, compound

HRID 1619399Notes

Reaction equation

HRID 1619399 reaction equation
O=[C:2]1[CH:10]([C:11]([O:13]CC)=O)[CH2:9][CH:8]2[N:4]([CH2:5][CH2:6][CH2:7]2)[CH2:3]1.[Br:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=1>ClCCCl.O>[Br:16][C:17]1[CH:22]=[CH:21][N:20]2[C:11](=[O:13])[C:10]3[CH2:9][CH:8]4[N:4]([CH2:5][CH2:6][CH2:7]4)[CH2:3][C:2]=3[N:23]=[C:19]2[CH:18]=1

Participants

5

Reactant 2

HCID 6932822-Amino-4-bromopyridineHCID 58574770HCID 58574770, compound

Product 1

HCID 58574592HCID 58574592, compoundYield 19.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 6-oxooctahydroindolizine-7-carboxylate (230 mg, 1.1 mmol), 4-bromopyridin-2-amine (188 mg, 1.1 mmol) and excess PPA (2 g) in 1,2-dichloroethane was stirred at 80° C. overnight. After the suspension was diluted with water (20 mL) and adjusted to pH 8. The mixture was extracted with ethyl acetate (3×50 mL) and the combined organic layers were concentrated to give the crude product. 70 mg of the desired product was obtained after column chromatography. MS (ESI): 320, 322 (MH+).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  2. concentrationthe combined organic layers were concentrated
  3. customto give the crude product

Sources & evidence

ORD record
ord-f994c76afdf04c5baa47969be0181757
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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