Methanol → N-[(2-Chloropyridin-4-yl)(2-cyano-3-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1662216노트

반응식

HRID 1662216 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=2[C:12]#[N:13])=O)[CH:5]=[CH:4][N:3]=1.[CH3:19][C:20]([S:23]([NH2:25])=[O:24])([CH3:22])[CH3:21].CO.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=2[C:12]#[N:13])=[N:25][S:23]([C:20]([CH3:22])([CH3:21])[CH3:19])=[O:24])[CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 3382465Tert-ButanesulfinamideHCID 585795302-(2-Chloro-pyridine-4-carbonyl)-6-fluorobenzonitrile

생성물 1

HCID 76821601N-[(2-Chloropyridin-4-yl)(2-cyano-3-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide수율 48%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ti(OEt)4 (15 mL) was added to a solution of 2-(2-chloro-pyridine-4-carbonyl)-6-fluoro-benzonitrile (3.6 g, 13.81 mmol) and 2-methyl-propane-2-sulfinic acid amide (2.5 g, 20.72 mmol) in dry THF (100 mL) at room temperature. The resulting mixture was stirred to reflux for 40 hours and then treated with CH3OH (50 mL) and saturated sodium bicarbonate solution (10 mL). The resulting suspension was filtered through a pad of Celite® and the solids were washed with THF (50 mL) and CH3OH (20 mL). The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography using a gradient of 25-50% EtOAc in hexane to afford the title compound (2.4 g, 48%).

후처리

  1. temperatureto reflux for 40 hours
  2. filtrationThe resulting suspension was filtered through a pad of Celite®
  3. washthe solids were washed with THF (50 mL) and CH3OH (20 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-541ade82e0ef4ed28067e695e121ca90
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030500B2

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