Sodium hydride → HCID 58382200、化合物

HRID 1627991ノート

反応式

HRID 1627991 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[C:10]([I:11])[C:3]=12.[H-].[Na+].[CH3:14][CH:15]([Si:17](Cl)([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[CH3:16]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si:17]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:16])[CH3:14])[CH:9]=[C:10]([I:11])[C:3]=12

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 115508744-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 58382200HCID 58382200、化合物収率 68.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The 4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (5.00 g, 17.9 mmol, US 2006128661 Example 1) in DMF (50 mL) was treated with 60 wt % NaH (0.790 g, 19.7 mmol) then stirred for about 15 min. The TIPSCl (4.18 mL, 19.8 mmol) was then added to the mixture and the mixture was stirred for about 30 min. The solvents were evaporated under reduced pressure then the material was partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (50 mL). The layers were separated then the aqueous layer was extracted with EtOAc (25 mL). The combined organics were washed with water (25 mL) then brine (25 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography using a 120 g silica column and eluting with heptane to give 4-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (5.34 g, 68%): LC/MS (Table 2, Method g) Rt=2.58 min; MS m/z 435 (M+H)+.

後処理

  1. stirringthe mixture was stirred for about 30 min
  2. customThe solvents were evaporated under reduced pressure
  3. customthe material was partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (50 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (25 mL)
  6. washThe combined organics were washed with water (25 mL)
  7. dry with materialbrine (25 mL), dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with heptane

出典と根拠

ORDレコード
ord-de1553cd484d47e7901d65214a23fd37
出典データセット
uspto-grants-2014_07
特許番号
US08785639B2

反応ノート

読み込み中…