Imidazole → 6-Bromo-2-(tert-butyldimethylsilyloxy)-N-methyl-1-naphthamide

HRID 480453ノート

反応式

HRID 480453 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([NH:14][CH3:15])=[O:13])=[C:7]([OH:16])[CH:6]=[CH:5]2.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].N1C=CN=C1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([NH:14][CH3:15])=[O:13])=[C:7]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:6]=[CH:5]2

参加物

4

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 187690866-Bromo-2-hydroxy-N-methyl-1-naphthamide

生成物 1

HCID 187691556-Bromo-2-(tert-butyldimethylsilyloxy)-N-methyl-1-naphthamide収率 94.6%

実験手順

A mixture of 6-bromo-2-hydroxy-N-methyl-1-naphthamide (2.50 g), tert-butyldimethylsilyl chloride (1.61 g), and imidazole (912 mg) in DMP (30 mL) was stirred for 2 h at room temperature. After dilution with water, the resulting mixture was extracted with AcOEt. The organic layer was washed with water and brine followed by concentrating in vacuo. The residue was passed through silica gel plug (hexane:AcOEt=1:1). The elute was concentrated, and the residue was washed with hexane to give the titled compound (3.33 g) as colorless needles.

後処理

  1. extractionAfter dilution with water, the resulting mixture was extracted with AcOEt
  2. washThe organic layer was washed with water and brine
  3. concentrationby concentrating in vacuo
  4. concentrationThe elute was concentrated
  5. washthe residue was washed with hexane

出典と根拠

ORDレコード
ord-1397b2e52e114acaaeff57aac996458b
出典データセット
uspto-grants-2003_11
特許番号
US06649643B1

反応ノート

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