Sodium hydride → 3-iodo-4-methoxy-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-c]pyridine

HRID 2206001ノート

反応式

HRID 2206001 の反応式
[I:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)(=O)=O)=CC=1>CN(C=O)C>[I:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:3]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 13961807Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonateHCID 247294143-Iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine

生成物 1

HCID 1179877623-iodo-4-methoxy-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-c]pyridine収率 61.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine (0.150 g) in DMF (10 mL) was added sodium hydride (60% dispersion in mineral oil, 55.0 mg), and the mixture was stirred at room temperature for 1 hr. Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate (0.351 g) was added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (120 mg).

後処理

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-76ea17d1eab942c5860eea30ac9e88a9
出典データセット
uspto-grants-2016_06
特許番号
US09371320B2

反応ノート

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