Oxalyl chloride → 7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carbonyl chloride

HRID 500765Notes

Reaction equation

HRID 500765 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14](O)=[O:15])[S:13][C:6]=12.C(Cl)(=O)C([Cl:27])=O>C(Cl)Cl>[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]([Cl:27])=[O:15])[S:13][C:6]=12

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 594245367-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxylic acid

Product 1

HCID 594245267-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carbonyl chlorideYield 104.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 39 (2.0 g, 5.98 mmol) in anhydrous CH2Cl2 (30 ml) under an atmosphere of nitrogen, was added oxalyl chloride (2.6 ml, 29.8 mmol). After stirring for 2 hours the solvent was evaporated, anhydrous toluene (10 mL) was added and the resultant mixture was evaporated (procedure of addition of toluene followed by evaporation was performed twice) to afford title compound 40 (2.2 g, 94% yield) as a white solid. The product was used without further purification and characterization and was assumed to be the mono-HCl salt.

Workup

  1. customwas evaporated
  2. additionanhydrous toluene (10 mL) was added
  3. customthe resultant mixture was evaporated (
  4. additionprocedure of addition of toluene
  5. customfollowed by evaporation

Sources & evidence

ORD record
ord-01c2737310004676bbc1cb3f233c6a30
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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