tert-Butylsulfinamide, (S)-(-)- → (NE)-N-[1-(6-bromo-3-pyridinyl)ethylidene]-2-methylpropane-2-sulfinamide

HRID 2038749노트

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HRID 2038749 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])C)=[CH:4][N:3]=1.[CH3:11][C:12]([S@@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>ClC(Cl)C.CCOCC.O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[N:3]=[CH:4][C:5](/[C:8](=[N:17]/[S:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])/[CH3:10])=[CH:6][CH:7]=1

참가 물질

7

반응물 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 206055102-Bromo-5-isopropylpyridine

생성물 1

HCID 88959185(NE)-N-[1-(6-bromo-3-pyridinyl)ethylidene]-2-methylpropane-2-sulfinamide수율 66%

시약·촉매·용매 4

HCID 76524Titanium tetraethoxide촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 63651,1-Dichloroethane용매

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온도
110 °C

실험 절차

To a solution of 2-bromo-5-isopropyl-pyridine (2.0 g, 9.99 mmol) in dichloroethane (15 mL) was added (S)-(−)-2-methyl-propane-2-sulfinic acid amide (1.45 g, 11.72 mmol) and titanium(IV) ethoxide (4.15 mL, 19.99 mmol). The mixture was heated at 110° C. in a microwave. After 2 h, the mixture was diluted with ether (20 mL) and water (6 mL). The mixture was stirred for 10 minutes. The layers were separated and the organic layer was dried over magnesium sulfate, filtered and concentrated to afford a residue. The crude residue was purified by normal phase flash chromatography on silica gel using ethyl acetate-dichloromethane (0-40%) to afford 2-methyl-propane-2-sulfinic acid[1-(6-bromo-pyridin-3-yl)-eth-(E)-ylidene]-amide (2.0 g, 66%).

후처리

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a residue
  6. customThe crude residue was purified by normal phase flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-89c91dda95c24d1fa97889aa73a130c2
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575360B2

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