Triethylsilane → Methyl 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

HRID 1036627ノート

反応式

HRID 1036627 の反応式
C([SiH](CC)CC)C.O=[C:9]([C:14]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11]>C(O)(C(F)(F)F)=O>[NH:16]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:22]2[C:14]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:15]1

参加物

4

反応物 2

HCID 12052TriethylsilaneHCID 6028556Methyl 7-azaindole-3-glyoxylate

生成物 1

HCID 25067325Methyl 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)acetate収率 75.2%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

To a mixture of triethylsilane (9.95 g, 85.78 mmol) in TFA (25 mL) was added portionwise methyl oxo(1H-pyrrolo[2,3-b]pyridin-3-yl)acetate (5.0 g, 24.48 mmol). After a period of 18 h at 50° C., the solvent was evaporated and saturated NaHCO3 was added followed by DCM. The organic phase was separated, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by combiflash with 10% ethyl acetate in hexane to 100% ethyl acetate to provide 3.5 g of the title compound.

後処理

  1. customthe solvent was evaporated
  2. additionsaturated NaHCO3 was added
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by combiflash with 10% ethyl acetate in hexane to 100% ethyl acetate

出典と根拠

ORDレコード
ord-47bde9a8ad6748d9986c78ccbceaf641
出典データセット
uspto-grants-2013_10
特許番号
US08546422B2

反応ノート

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