Sodium Chlorite → 1-Benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid

HRID 2384495ノート

反応式

HRID 2384495 の反応式
[CH2:1]([N:8]1[C:12]2=[CH:13][N:14]=[C:15]([O:17][CH3:18])[CH:16]=[C:11]2[C:10]([CH:19]=[O:20])=[C:9]1[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:24]Cl=O.[Na+]>CC(O)(C)C.CC(=CC)C.O>[CH2:1]([N:8]1[C:12]2=[CH:13][N:14]=[C:15]([O:17][CH3:18])[CH:16]=[C:11]2[C:10]([C:19]([OH:24])=[O:20])=[C:9]1[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 2

HCID 23668197Sodium Chlorite2 回HCID 446084491-Benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde2 回

生成物 1

HCID 446086091-Benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6386tert-Butanol溶媒HCID 105532-Methyl-2-butene溶媒2 回

実験手順

To a solution of 1-benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde (Compound 7, 20 mg, 0.065 mmol) in t-BuOH (1.5 ml) and 2-methyl-2-butene (1 ml) was added a solution of NaH2PO4 (94 mg, 0.78 mmol) and NaClO2 (80%, 73 mg, 0.65 mmol) in H2O (1.5 ml). The mixture was stirred at room temperature and additional 2-methyl-2-butene and a solution of NaH2PO4 and NaClO2 in H2O were added at the above ratio every 6-16 h until the progress of the reaction was satisfactory. The reaction mixture was extracted with EtOAc (×3) and the combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (PTLC) on silica gel (50% EtOAc-hexanes) to yield the title compound.

後処理

  1. extractionThe reaction mixture was extracted with EtOAc (×3)
  2. washthe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (PTLC) on silica gel (50% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-9d2cf312e8bd4b68b5db2c8179b5859a
出典データセット
uspto-grants-2012_09
特許番号
US08263767B2

反応ノート

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