Water → HCID 117993037、化合物

HRID 922582ノート

反応式

HRID 922582 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([Cl:11])[CH:3]=1.O.[OH-].[Cs+].[CH3:15]I.O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:15])=[C:4]([Cl:11])[CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 23679066Caesium hydroxide--water (1/1/1)HCID 247280986-Bromo-4-chloro-1H-indazole

生成物 1

HCID 117993037HCID 117993037、化合物収率 62%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of 6-bromo-4-chloro-1H-indazole (4.0 g, 17.4 mmol), cesium hydroxide monohydrate (23.3 g, 139 mmol), tetrabutylammonium hydrogensulfate (1.36 g, 3.99 mmol) in anhydrous THF (80 mL) was added a solution of methyl iodide (9.86 g, 69.4 mmol) in THF (10 mL) dropwise at r.t. The reaction mixture was stirred for 15 min at r.t. Water was added to the reaction mixture, and the aqueous layer was extracted with EtOAc. The organic layer was concentrated, and the crude reside was purified by silica gel column chromatography (EtOAc/Heptane 0 to 100% gradient as eluent) to afford 6-Bromo-4-chloro-1-methyl-1H-indazole (2.65 g, 62%). 1H NMR (600 MHz, methanol-d4) δ 4.05 (s, 3H), 7.32 (d, 1H), 7.79 (s, 1H), 8.03 (s, 1H).

後処理

  1. extractionthe aqueous layer was extracted with EtOAc
  2. concentrationThe organic layer was concentrated
  3. customthe crude reside was purified by silica gel column chromatography (EtOAc/Heptane 0 to 100% gradient as eluent)

出典と根拠

ORDレコード
ord-2c9b8e943a9c40038517396a17c26fc1
出典データセット
uspto-grants-2016_03
特許番号
US09278953B2

反応ノート

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