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

HRID 2038749ノート

反応式

HRID 2038749 の反応式
[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

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 76524Titanium tetraethoxide触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
110 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-89c91dda95c24d1fa97889aa73a130c2
出典データセット
uspto-grants-2013_11
特許番号
US08575360B2

反応ノート

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