2-Amino-5-bromopyridine → HCID 178426926, compound

HRID 1181549Notes

Reaction equation

HRID 1181549 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C[Al](C)C.C([O:15][C:16]([C:18]1[NH:22][N:21]=[C:20]([CH3:23])[CH:19]=1)=O)C>C(Cl)Cl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:16]([C:18]2[NH:22][N:21]=[C:20]([CH3:23])[CH:19]=2)=[O:15])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 706222-Amino-5-bromopyridineHCID 16682925TrimethylaluminumHCID 178469061HCID 178469061, compound

Product 1

HCID 178426926HCID 178426926, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-amino-5-bromopyridine (0.200 g, 1.16 mmol 1.0 equiv), in 5 mls of methylene chloride, under argon, was treated with trimethylaluminum (0.312 mL, 2.0N in hexanes, 4.0 equiv) at room temperature for 30 min. To the solution was added ethyl-3-methylpyrazole-5-carboxylate (0.356 g, 2.0 equiv). After 4 hrs, the volatile was evaporated, and the residue was redissolved into EtOAc, washed with 0.5N HCl, 0.2 N K2CO3, and saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered, evaporated and purified via flash chromatography on silica gel to give N-(5-bromo-2-pyridinyl)-(3-methyl)-5-pyrazolecarboxamide (0.160 g, 49%). MS found for C10H9BrN4O (M+H)+: 281, 283.

Workup

  1. customthe volatile was evaporated
  2. dissolutionthe residue was redissolved into EtOAc
  3. washwashed with 0.5N HCl, 0.2 N K2CO3, and saturated aqueous NaCl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. custompurified via flash chromatography on silica gel

Sources & evidence

ORD record
ord-3583181ee6084b4da2519154f7028b81
Source dataset
uspto-grants-2007_10
Patent number
US07285565B2

Reaction notes

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