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Cesium carbonate → tert-butyl 1-(1-cyclopropyl-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 1527085
ノート
印刷プレビュー

反応式

HRID 1527085 の反応式
[CH3:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Br[CH:19]([CH3:25])[C:20]([CH:22]1[CH2:24][CH2:23]1)=[O:21].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:22]1([C:20](=[O:21])[CH:19]([N:10]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[C:3]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[C:2]2[CH3:1])[CH3:25])[CH2:24][CH2:23]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 450808052-Bromo-1-cyclopropylpropan-1-oneHCID 89739113tert-Butyl 2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

生成物 1

HCID 117778856tert-butyl 1-(1-cyclopropyl-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate収率 54%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

実験手順

The solution of tert-butyl 2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (300.00 mg, 1.29 mmol), 2-bromo-1-cyclopropylpropan-1-one (342.98 mg, 1.94 mmol), Cs2CO3 (841.63 mg, 2.58 mmol), KI (42.88 mg, 0.26 mmol) in DMF (4 ml) were stirred at 25° C. for 18 h. After the reaction completed, the solution was partitioned between EtOAc and H2O. The organic layer was separated, dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by flash column (Eluent: PE:EtOAc=10:1) to get tert-butyl 1-(1-cyclopropyl-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate as a white oil. (230 mg, yield 54%).

後処理

  1. customthe solution was partitioned between EtOAc and H2O
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash column (Eluent: PE:EtOAc=10:1)

出典と根拠

ORDレコード
ord-4c3ec8078180404391740d6ba513d7da
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085583B2

反応ノート

読み込み中…

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