Diisopropylethylamine → 1H-Pyrrolo[2,3-b]pyridine, 6-bromo-1-[tris(1-methylethyl)silyl]-

HRID 1098506ノート

反応式

HRID 1098506 の反応式
[Br:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Si:20](OS(C(F)(F)F)(=O)=O)([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22]>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 111599156-Bromo-7-azaindole

生成物 1

HCID 580876901H-Pyrrolo[2,3-b]pyridine, 6-bromo-1-[tris(1-methylethyl)silyl]-

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

6-bromo-1H-pyrrolo[2,3-b]pyridine (587, 275 mg, 1.39 mmol) was dissolved in 4 mL of dry dioxane. DIEA (3 equiv) and TIPS-OTf (2.5 equiv) were added and the reaction was stirred at 50° C. overnight. The reaction was then diluted with 20 mL of ethyl acetate and washed 2 times with 10 mL NaHCO3 (aq., 5%) and once with 10 mL brine. The organic fraction was dried over MgSO4, evaporated and diluted with 5.5 mL of dry toluene 10 mg bromide per 0.2 mL of solution) to use directly in the next reaction step.

後処理

  1. washwashed 2 times with 10 mL NaHCO3 (aq., 5%)
  2. dry with materialThe organic fraction was dried over MgSO4
  3. customevaporated
  4. additiondiluted with 5.5 mL of dry toluene 10 mg bromide per 0.2 mL of solution)
  5. customto use directly in the next reaction step

出典と根拠

ORDレコード
ord-26db3e664336498ab8c6b133e465834f
出典データセット
uspto-grants-2012_03
特許番号
US08143271B2

反応ノート

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