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

HRID 1445941ノート

反応式

HRID 1445941 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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%

後処理

  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)

出典と根拠

ORDレコード
ord-5786cab8981c45ff8b531f00a4aa56a0
出典データセット
uspto-grants-2010_02
特許番号
US07666898B2

反応ノート

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