Triisopropylsilyl chloride → HCID 59540525、化合物

HRID 1677381

反応式

HRID 1677381 の反応式
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[N:9]=2)[NH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl[Si:34]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36]>O1CCCC1>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[N:9]=2)[N:4]([Si:34]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36])[CH:3]=1

参加物

5

反応物 3

HCID 139400Triisopropylsilyl chloride2 回HCID 3251421Potassium bis(trimethylsilyl)amideHCID 595405187-iodo-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

生成物 1

HCID 59540525HCID 59540525、化合物収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 7-iodo-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (6.7 g, 16.29 mmol) in anhydrous tetrahydrofuran (150 ml) was cooled to 0° C. and treated with potassium bis(trimethylsilyl)amide (0.5M in toluene, 35.85 ml, 17.9 mmol) dropwise. After complete addition, the reaction mixture was stirred at room temperature for 1 hour, treated dropwise with chloro-triisopropyl-silane (3.9 ml, 18.4 mmol), and allowed to stir at room temperature for 16 hours. Chloro-triisopropyl-silane (1.0 ml, 4.7 mmol) was added, and the reaction mixture was stirred at room temperature for 16 hours, and then at 60° C. for 16 hours. The reaction mixture was partitioned between EtOAc/saturated aqueous NH4Cl. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a dark solid. The residue was purified by silica gel chromatography using 3-100% EtOAc in hexanes as eluant to provide 7.4 g (80%) of 7-iodo-5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine as a white solid. MP 156.5-157.2, M+H=568.

後処理

  1. additionAfter complete addition
  2. stirringto stir at room temperature for 16 hours
  3. stirringthe reaction mixture was stirred at room temperature for 16 hours
  4. waitat 60° C. for 16 hours
  5. customThe reaction mixture was partitioned between EtOAc/saturated aqueous NH4Cl
  6. customThe organic layers were collected
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customgiving a dark solid
  11. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-d5739315710440908019fe714f8e21ef
出典データセット
uspto-grants-2011_08
特許番号
US08008298B2

関連ノート

読み込み中…