Water → HCID 86694712, 화합물

HRID 475164노트

반응식

HRID 475164 반응식
[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

참가 물질

7

반응물 4

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

생성물 2

HCID 712720841425932-77-9수율 12%HCID 86694712HCID 86694712, 화합물수율 58%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-79efe1a1b6df4d8b810747b5840bb029
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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