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Dichloromethane → HCID 58010001、化合物

HRID 1628056
ノート
印刷プレビュー

反応式

HRID 1628056 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21]O)[N:20]=[C:15]2[CH:14]=1.C(Cl)Cl.S(Cl)(Cl)=O.[N-:39]=[N+:40]=[N-:41].[Na+]>O>[N:39]([CH2:21][C:19]1[N:20]=[C:15]2[CH:14]=[C:13]([C:6]3[C:5]4[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=4)[N:8]([CH3:12])[CH:7]=3)[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:31])[CH3:30])[C:16]2=[N:17][CH:18]=1)=[N+:40]=[N-:41]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 58009987HCID 58009987、化合物

生成物 1

HCID 58010001HCID 58010001、化合物収率 100%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A flask was charged with (6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanol (4.00 g, 9.12 mmol, Preparation #F.1), DCM (90 mL) and thionyl chloride (0.732 mL, 10.0 mmol). The mixture was stirred at rt for about 40 min and concentrated under reduced pressure. The residue was dissolved in DMF (90 mL) and treated with NaN3 (1.48 g, 22.8 mmol). The mixture was stirred overnight at rt. The solution was diluted with water (150 mL). The suspension was extracted with EtOAc (3×125 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give 2-(azidomethyl)-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (4.23 g, 100%): LC/MS (Table 2, Method b) Rt=3.16 min; MS m/z 464 (M+H)+.

後処理

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in DMF (90 mL)
  3. stirringThe mixture was stirred overnight at rt
  4. extractionThe suspension was extracted with EtOAc (3×125 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-6e5a3d837b54418b80c1b2efed896284
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785639B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート