Sodium Sulfite → 2-Bromo-5-(5-chloro-2-fluoro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

HRID 2204342ノート

反応式

HRID 2204342 の反応式
[O-]S([C:5]([F:8])(F)F)(=O)=O.F[N+]1C(C)=CC(C)=CC=1C.[Br:19][C:20]1[N:24]([CH:25]([CH3:27])[CH3:26])[C:23]2[CH:28]([C:41]3[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=3)[N:29]([C:32]3[CH:37]=[C:36]([Cl:38])[C:35](=[O:39])[N:34](C)[CH:33]=3)[C:30](=[O:31])[C:22]=2[CH:21]=1.S([O-])([O-])=O.[Na+].[Na+]>ClCCCl>[Br:19][C:20]1[N:24]([CH:25]([CH3:27])[CH3:26])[C:23]2[CH:28]([C:41]3[CH:42]=[CH:43][C:44]([Cl:47])=[CH:45][CH:46]=3)[N:29]([C:32]3[CH:37]=[C:36]([Cl:38])[C:35](=[O:39])[N:34]([CH3:33])[C:5]=3[F:8])[C:30](=[O:31])[C:22]=2[CH:21]=1

参加物

5

反応物 3

HCID 24437Sodium SulfiteHCID 27245751-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent]HCID 867031442-bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one2 回

生成物 1

HCID 867031432-Bromo-5-(5-chloro-2-fluoro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

1-Fluoro-2,4,6-trimethyl-pyridinium triflate [107264-00-6] (1.476 mmol) was added to a solution of 2-bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Intermediate E) (0.738 mmol) in 1,2-dichloroethane (12 mL) and then the mixture was heated to 80° C. in the dark. After 12 h, the reaction mixture was cooled to rt, poured into a 2% aqueous solution of sodium sulfite and extracted with EtOAc (2×). The combined organic layers were successively washed with 1M aqueous citric acid, 1M aqueous NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a pink foam. ESI-MS: tR=1.16 min, [M]+ 512/514/516 (LC-MS 1); TLC: Rf=0.10 (1.1 EtOAc/heptanes).

後処理

  1. temperaturethe reaction mixture was cooled to rt
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were successively washed with 1M aqueous citric acid, 1M aqueous NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified

出典と根拠

ORDレコード
ord-d7d9ac53f51748369a5f16555c475a0d
出典データセット
uspto-grants-2016_06
特許番号
US09365576B2

反応ノート

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