Oxalyl chloride → 5-[2-(4-bromo-2-chloro-phenyl)-acetyl]-1-methyl-1H-pyridin-2-one

HRID 333867ノート

反応式

HRID 333867 の反応式
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9]([OH:11])=O)=[CH:3]1.C(Cl)(=O)C(Cl)=O.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[C:21]([Cl:27])[CH:20]=1>C(Cl)Cl.CN(C)C=O.COCCOC.[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:9]([C:4]2[CH:5]=[CH:6][C:7](=[O:8])[N:2]([CH3:1])[CH:3]=2)=[O:11])=[C:21]([Cl:27])[CH:20]=1

参加物

9

反応物 3

HCID 65578Oxalyl chlorideHCID 592704N(1)-methyl-2-pyridone-5-carboxylic acidHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzene

生成物 1

HCID 666994925-[2-(4-bromo-2-chloro-phenyl)-acetyl]-1-methyl-1H-pyridin-2-one

試薬・触媒・溶媒 5

HCID 6228Dimethylformamide触媒HCID 23994Zinc触媒HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒HCID 80711,2-Dimethoxyethane溶媒3 回

実験手順

To a suspension of 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (606 mg) in CH2Cl2 (5 ml) were added one drop of N,N-dimethylformamide and oxalylchloride (803 mg). The mixture was stirred at room temperature for 1.5 h and was then concentrated to dryness. 1,2-Dimethoxyethane was added and the solvent was evaporated again to give the crude acid chloride. To a suspension of zinc powder (517 mg) in 1,2-dimethoxyethane (5 ml) was added tetrakis(triphenylphosphine)palladium(0) (55 mg). A suspension of the acid chloride in 1,2-dimethoxyethane (5 ml) was added. The mixture was cooled in an ice bath and a solution of 4-bromo-1-bromomethyl-2-chloro-benzene (1.125 g) in 1,2-dimethoxyethane (5 ml) was slowly added over 30 min. The mixture was stirred for 30 min at 0° C. and for 1.5 h at room temperature. The mixture was filtered and the filtrate was concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 7:3=>0:1) to give the title compound (603 mg, not completely pure) as a colorless solid. MS (m/e, ISP neg. ion)=338.0 [M−H+].

後処理

  1. concentrationwas then concentrated to dryness
  2. addition1,2-Dimethoxyethane was added
  3. customthe solvent was evaporated again
  4. customto give the crude acid chloride
  5. additionwas added
  6. temperatureThe mixture was cooled in an ice bath
  7. stirringThe mixture was stirred for 30 min at 0° C. and for 1.5 h at room temperature
  8. filtrationThe mixture was filtered
  9. concentrationthe filtrate was concentrated
  10. customThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 7:3=>0:1)

出典と根拠

ORDレコード
ord-e70df52edb37436fb7bab02b5d5cda3c
出典データセット
uspto-grants-2014_11
特許番号
US08883786B2

反応ノート

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