Water → 1-(benzenesulfonyl)-2-ethynyl-1H-pyrrolo[2,3-b]pyridine

HRID 2196731노트

반응식

HRID 2196731 반응식
C(=O)([O-])[O-].[K+].[K+].[C:7]1([S:13]([N:16]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=[C:17]2[CH:25]=O)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N+](=[C:29](P(=O)(OC)OC)C(=O)C)=[N-].O>CO.C(OCC)(=O)C>[C:25]([C:17]1[N:16]([S:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:15])=[O:14])[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH:18]=1)#[CH:29]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 566921991-(Phenylsulfonyl)-1H-pyrrolo(2,3-b)pyridine-2-carboxaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

생성물 1

HCID 730135321-(benzenesulfonyl)-2-ethynyl-1H-pyrrolo[2,3-b]pyridine수율 41%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 8857Ethyl Acetate용매

실험 절차

Potassium carbonate (0.97 g, 6.98 mmol) was added to a suspension of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (1.00 g, 3.49 mmol) in methanol (1.0 mL), followed by the addition of a solution of dimethyl 1-diazo-2-oxopropylphosphonate (0.81 g, 4.19 mmol) in methanol (0.2 mL). The reaction mixture was stirred at room temperature for 2 hours, after which water was added, then ethyl acetate. The layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude was purified by flash chromatography to afford 2-ethynyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.40 g, 41%; purity 70%).

후처리

  1. customThe layers were separated
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialThe organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by flash chromatography

출처 및 근거

ORD 기록
ord-5e9e552f5a58458693df8b5aebb59c50
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338452B2

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