Chlorotrimethylsilane → 4-bromo-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1180957ノート

反応式

HRID 1180957 の反応式
C(NC(C)C)(C)C.[Li]CCCC.[Br:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[N:20]([S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:21]=[CH:22][C:15]=12.Cl[Si:33]([CH3:36])([CH3:35])[CH3:34]>C1COCC1>[Br:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[N:20]([S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:21]([Si:33]([CH3:36])([CH3:35])[CH3:34])=[CH:22][C:15]=12

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 450745614-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridineHCID 178418339Butyllithium

生成物 1

HCID 689992204-bromo-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of N,N-diisopropylamine (3.6 mmol) in THF (9 ml) was cooled to −78° C. under a nitrogen atmosphere. A solution of n-BuLi (2.5M in hexanes, 3.3 mmol) was added dropwise over 3 minutes. After 30 minutes of stirring, a solution of 4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (3.1 mmol) in THF (9 ml) was added dropwise over 9 minutes. After an additional 2 hours of stirring at −78° C., chlorotrimethylsilane (3.1 mmol) was added dropwise over 1 minute. After 1 hour of stirring at −78° C., the reaction was quenched with saturated NH4Cl(aq) (10 ml), warmed to room temperature, and partitioned between water and EtOAc. The aqueous phase was further extracted with EtOAc and the organic layers combined, washed with brine, dried (MgSO4), concentrated, and purified by silica gel chromatography (isocratic CHCl3) to give the title product as a white solid (82%). ESMS [M+H]+: 410.8.

後処理

  1. stirringAfter an additional 2 hours of stirring at −78° C.
  2. stirringAfter 1 hour of stirring at −78° C.
  3. customthe reaction was quenched with saturated NH4Cl(aq) (10 ml)
  4. custompartitioned between water and EtOAc
  5. extractionThe aqueous phase was further extracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (isocratic CHCl3)

出典と根拠

ORDレコード
ord-305875df41c7433bb16304fd61758529
出典データセット
uspto-grants-2007_10
特許番号
US07282588B2

反応ノート

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