Water → HCID 86694712、化合物

HRID 475164ノート

反応式

HRID 475164 の反応式
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[H-].[Na+].I[CH3:15].O>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH3:15].[Br:1][C:2]1[C:3]2[C:7]([CH:8]=[C:9]([F:11])[CH:10]=1)=[N:6][N:5]([CH3:15])[CH:4]=2

参加物

7

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 247287454-Bromo-6-fluoro-1H-indazole

生成物 2

HCID 712720841425932-77-9収率 12%HCID 86694712HCID 86694712、化合物収率 58%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-bromo-6-fluoro-1H-indazole (2.3 g, 10.7 mmol) in anhydrous DMF (36 mL) was added sodium hydride (60% dispersion in mineral oil, 0.51 g, 12.8 mmol, 1.2 eq.). After stirring at RT for 5 min, iodomethane (2.2 mL) was added, and the resulting mixture was stirred at RT overnight. The reaction mixture was poured into water (200 mL) and extracted with EtOAc (2×100 mL). The combined extracts were washed with water (200 mL) and brine (50 mL), dried (MgSO4), filtered, and evaporated in vacuo. The residue was purified by SiO2 chromatography eluting with hexane:EtOAc (3:1) to afford 4-bromo-6-fluoro-1-methyl-1H-indazole as a tan solid (1.42 g, 58%) and 4-bromo-6-fluoro-2-methyl-2H-indazole (0.29 g, 12%) as a tan solid. MS (ESI): m/z=229.1 [M+1]+.

後処理

  1. stirringthe resulting mixture was stirred at RT overnight
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined extracts were washed with water (200 mL) and brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by SiO2 chromatography
  8. washeluting with hexane:EtOAc (3:1)

出典と根拠

ORDレコード
ord-79efe1a1b6df4d8b810747b5840bb029
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

読み込み中…