Dimethylformamide → HCID 22467331, compound

HRID 1934731Notes

Reaction equation

HRID 1934731 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8](=[O:18])[C:9]2[CH:14]=[C:13]([CH:15]=[CH2:16])[CH:12]=[CH:11][C:10]=2[F:17])=[CH:4][C:3]=1[O:21][CH3:22].CN(C)C=[O:26]>O.[Cu]Cl.[Pd](Cl)Cl>[C:15]([C:13]1[CH:12]=[CH:11][C:10]([F:17])=[C:9]([CH:14]=1)[C:8]([NH:7][CH2:6][C:5]1[CH:19]=[CH:20][C:2]([Cl:1])=[C:3]([O:21][CH3:22])[CH:4]=1)=[O:18])(=[O:26])[CH3:16]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 22467621HCID 22467621, compound

Product 1

HCID 22467331HCID 22467331, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of copper(I) chloride (464 mg) and palladium(II) chloride (83.2 mg) in a mixture of dimethylformamide (42 mL) and water (6 mL) was stirred for an hour under oxygen atmosphere (1 atm) at ambient temperature. To the mixture was added N-(4-chloro-3-methoxybenzyl)-2-fluoro-5-vinylbenzamide (1.50 g). After stirring for 6 hours at 60° C., the mixture was partitioned between ethyl acetate and 1N-hydrochoric, acid. The separated organic layer was washed with water, an aqueous saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (2:1 to 1:1) to give 5-acetyl-2-fluoro-N-(4-chloro-3-methoxybenzyl)benzamide as colorless powders (719 mg).

Workup

  1. stirringAfter stirring for 6 hours at 60° C.
  2. customthe mixture was partitioned between ethyl acetate and 1N-hydrochoric, acid
  3. washThe separated organic layer was washed with water
  4. dry with materialan aqueous saturated sodium bicarbonate solution and brine, dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by a silica gel column chromatography
  7. washeluting with a mixture of hexane and ethyl acetate (2:1 to 1:1)

Sources & evidence

ORD record
ord-9455ae668d744d1bad2e32e5815974f9
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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