Triacetoxyperiodinane → 2-(3-bromo-quinolin-6-yloxy)-N-(1,1-dimethyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide

HRID 1892040ノート

反応式

HRID 1892040 の反応式
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH:13]([S:22][CH3:23])[C:14]([NH:16][C:17]([CH3:21])([CH3:20])[CH2:18][OH:19])=[O:15])=[CH:7][CH:6]=2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH:13]([S:22][CH3:23])[C:14]([NH:16][C:17]([CH3:20])([CH3:21])[CH:18]=[O:19])=[O:15])=[CH:7][CH:6]=2

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 667178702-(3-bromo-quinolin-6-yloxy)-N-(2-hydroxy-1,1-dimethyl-ethyl)-2-methylsulfanyl-acetamide

生成物 1

HCID 866480202-(3-bromo-quinolin-6-yloxy)-N-(1,1-dimethyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide収率 94.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(3-Bromo-quinolin-6-yloxy)-N-(2-hydroxy-1,1-dimethyl-ethyl)-2-methylsulfanyl-acetamide (0.2 g) from Stage 2, Step 1 above in dichloromethane (15 ml) was treated with Dess-Martin periodinane (0.42 g). The reaction mixture was stirred at rt for 1 hour. The reaction mixture was quenched with sat. aqueous NaHCO3 and sat. aqueous sodium thiosulphate. The reaction mixture was vigorously stirred at rt. for 30 minutes after which time the two phases were separated. The organic layer was washed with sat. aqueous. NaHCO3. After separation the organic phase was dried over magnesium sulphate, filtered and evaporated. The residue was purified by column chromatography (heptane/ethyl acetate 1:1) to give 2-(3-bromo-quinolin-6-yloxy)-N-(1,1-dimethyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide as white solid (0.188 g). 1H NMR (CDCl3) δ ppm: 9.41 (1H, s); 8.83 (1H, d); 8.26 (1H, d); 8.08 (1H, d); 7.51 (1H, dd); 7.22 (1H, d); 5.69 (1H, s); 2.20 (3H, s); 1.53 (6H, s).

後処理

  1. customThe reaction mixture was quenched with sat. aqueous NaHCO3 and sat. aqueous sodium thiosulphate
  2. stirringThe reaction mixture was vigorously stirred at rt
  3. customfor 30 minutes after which time the two phases were separated
  4. washThe organic layer was washed with sat. aqueous
  5. customAfter separation the organic phase
  6. dry with materialwas dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography (heptane/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-a2a9304921e04a3882deeba7354587f0
出典データセット
uspto-grants-2013_08
特許番号
US08507509B2

反応ノート

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