Potassium tert-butoxide → 4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

HRID 1445941노트

반응식

HRID 1445941 반응식
C([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([O:17][CH3:18])[C:11]=2[CH:10]=[C:9]1[CH3:19])C1C=CC=CC=1.CC(C)([O-])C.[K+]>C1COCC1>[CH3:18][O:17][C:12]1[C:11]2[CH:10]=[C:9]([CH3:19])[NH:8][C:16]=2[CH:15]=[CH:14][N:13]=1

참가 물질

4

반응물 2

HCID 23665647Potassium tert-butoxideHCID 591703081-benzyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

생성물 1

HCID 534128814-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 1-benzyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine (2) (0.887 g, 3.51 mmole) in anhydrous THF (10 mL) dimethyl sulfoxide (25 mL) was added slowly (via a syringe) and the mixture was cooled to 0° C. Potassium tert-butoxide (1M in THF, 25 mL, 25 mmole) was added slowly. Oxygen was bubbled through the mixture for 45 minutes. The reaction was quenched with saturated ammonium chloride solution, the mixture was extracted with ethyl acetate (3×50 mL). The organic layer was separated, dried over magnesium sulphate and concentrated. The residue was purified by column chromatography (3:1 Hex:EtOAc) to afford intermediate (3). Yield: 1.06 g >100%

후처리

  1. customOxygen was bubbled through the mixture for 45 minutes
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (3:1 Hex:EtOAc)

출처 및 근거

ORD 기록
ord-5786cab8981c45ff8b531f00a4aa56a0
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666898B2

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