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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
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HRID 1527085 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-4c3ec8078180404391740d6ba513d7da
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085583B2

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