Oxalyl chloride → 6-bromo-3-benzyloxy-4-methoxypyridine-2-carbonyl Chloride

HRID 1797025Notes

Reaction equation

HRID 1797025 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](O)=[O:9])[C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([O:19][CH3:20])[CH:3]=1.C(Cl)(=O)C([Cl:24])=O>C1C=CC=CC=1.CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]([Cl:24])=[O:9])[C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([O:19][CH3:20])[CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 22175084HCID 22175084, compound

Product 1

HCID 221750736-bromo-3-benzyloxy-4-methoxypyridine-2-carbonyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

To a stirred mixture of 16 (2.54 g., 7.5 mmol) in benzene (30 mL) containing DMF (3 drops) was added oxalyl chloride (1.90 g, 15 mmol) in one portion. After gas evolution had ceased (about 45 min.), the now homogeneous solution was stirred an additional 15 min., then the solvent was evaporated. 1,2-dichloroethane (30 mL) was added and again the solvent was evaporated to give a quantitative yield of 3 as a nearly colorless oil. This material was dissolved in CH2Cl2 (10 mL) or THF (10 mL) and used directly in subsequent coupling reactions. 6-Bromo-3-Hydroxypicolinic Acid (17).

Workup

  1. custom(about 45 min.)
  2. customthe solvent was evaporated
  3. addition1,2-dichloroethane (30 mL) was added
  4. customagain the solvent was evaporated

Sources & evidence

ORD record
ord-a3eb641db63a4490a6b040ecbfc66d77
Source dataset
uspto-grants-2006_04
Patent number
US07034035B2

Reaction notes

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