Dimethylformamide → HCID 178434462、化合物

HRID 643976ノート

反応式

HRID 643976 の反応式
[Li]C(C)(C)C.Br[C:7]1[CH:8]=[C:9]2[C:15]([CH3:16])=[N:14][NH:13][C:10]2=[N:11][CH:12]=1.CN([CH:20]=[O:21])C>C1COCC1>[CH3:16][C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([CH:20]=[O:21])[CH:8]=2)[NH:13][N:14]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 178418306HCID 178418306、化合物HCID 178434433HCID 178434433、化合物

生成物 1

HCID 178434462HCID 178434462、化合物収率 20.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

80 ml anhydrous THF were charged into a 250 ml round bottom flask and was chilled to −78° C. t-BuLi (1.70 M in THF, 17.6 ml, 30 mmol) was added to the flask via syringe. After stirring for 5 min, 5-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine (2.12 g, 10 mmol) was added dropwise via syringe. After 30 min, DMF (3.65 g, 50 mmol) in 20 ml THF was added dropwise and the mixture was stirred for overnight. The reaction was quenched by saturated aqueous ammonium chloride. After evaporating the excess THF, the reaction mixture was extracted by ethylacetate twice. The combined organic layer was washed with brine once and dried over sodium sulfate. The crude product was chromatographed with 50% ethylacetate in hexane to afford the desired product (0.23 g, y=20.5%).

後処理

  1. additionwas added to the flask via syringe
  2. waitAfter 30 min
  3. stirringthe mixture was stirred for overnight
  4. customThe reaction was quenched by saturated aqueous ammonium chloride
  5. customAfter evaporating the excess THF
  6. extractionthe reaction mixture was extracted by ethylacetate twice
  7. washThe combined organic layer was washed with brine once
  8. dry with materialdried over sodium sulfate
  9. customThe crude product was chromatographed with 50% ethylacetate in hexane

出典と根拠

ORDレコード
ord-81548312bb9a4418a7d6fc4913a9d59d
出典データセット
uspto-grants-2010_04
特許番号
US07700636B2

反応ノート

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