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 2204342노트

반응식

HRID 2204342 반응식
[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

참가 물질

5

반응물 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-one2회

생성물 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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d7d9ac53f51748369a5f16555c475a0d
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365576B2

반응 노트

불러오는 중…