Sodium Bicarbonate → N-((5-chloro-2-cyano-3-fluorophenyl)(3-methoxyphenyl)methylene)-2-methylpropane-2-sulfinamide

HRID 1662222

반응식

HRID 1662222 반응식
[Cl:1][C:2]1[CH:9]=[C:8]([C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:5]([C:6]#[N:7])=[C:4]([F:20])[CH:3]=1.[CH3:21][C:22]([S:25]([NH2:27])=[O:26])([CH3:24])[CH3:23].C([O-])(O)=O.[Na+]>C1COCC1.C(Cl)Cl.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Cl:1][C:2]1[CH:3]=[C:4]([F:20])[C:5]([C:6]#[N:7])=[C:8]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[N:27][S:25]([C:22]([CH3:24])([CH3:23])[CH3:21])=[O:26])[CH:9]=1

참가 물질

7

반응물 3

HCID 516892Sodium BicarbonateHCID 3382465Tert-ButanesulfinamideHCID 585795244-Chloro-2-fluoro-6-(3-methoxybenzoyl)benzonitrile

생성물 1

HCID 76821604N-((5-chloro-2-cyano-3-fluorophenyl)(3-methoxyphenyl)methylene)-2-methylpropane-2-sulfinamide수율 59%

시약·촉매·용매 3

HCID 76524Titanium tetraethoxide촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

4-Chloro-2-fluoro-6-(3-methoxybenzoyl)benzonitrile (2.56 g, 8.84 mmol), 2-methyl-2-propanesulfinamide (1.392 g, 11.49 mmol) and titanium(IV) ethoxide (4.62 mL, 22.09 mmol) were dissolved in THF (30 mL) and stirred at 75° C. over weekend. When cooled to rt, the mixture was diluted with DCM (25 mL). Saturated aqueous NaHCO3 (3 mL) was added followed by silica and the mixture concentrated under reduced pressure until a free flowing powder was obtained. Purification on a silica gel column (0-40% EtOAc in heptane as eluent) gave 2.04 g (59% yield) of the title compound.

후처리

  1. temperatureWhen cooled to rt
  2. concentrationthe mixture concentrated under reduced pressure until
  3. customwas obtained
  4. customPurification on a silica gel column (0-40% EtOAc in heptane as eluent)

출처 및 근거

ORD 기록
ord-751b48230fcf4f98beb5a0f168bc0b32
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030500B2

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