Water → HCID 67259108, compound

HRID 2359106Notes

Reaction equation

HRID 2359106 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.N1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH2:15]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:10](=[O:15])[CH2:11][CH:12]2[CH2:14][CH2:13]2)[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 6932822-Amino-4-bromopyridine

Product 1

HCID 67259108HCID 67259108, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyclopropylacetic acid (250 mmol) in DCM was added 1 mL of DMF. Oxalyl chloride (312 mmol) was added dropwise and the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated to afford 30.3 g of the crude acid chloride that was added dropwise to a solution of 4-bromo-2-aminopyridine (202 mmol) and pyridine (506 mol) in 500 mL dichloromethane. The reaction mixture was stirred at room temperature for 4 h. Water was added and the reaction mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by chromatography on silica gel to afford 26.0 g of N-(4-bromopyridin-2-yl)-2-cyclopropylacetamide (50% yield).

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-6e4eb37f1beb4d75b0d9e2fbf6309cc5
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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