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

HRID 277142Notes

Reaction equation

HRID 277142 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.

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-7cbdd84a1b124ae283b0c12347dc3e9c
Source dataset
uspto-grants-2002_03
Patent number
US06355660B1

Reaction notes

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