Hydrazine hydrate (1:1) → 5-[(3,5-difluorophenyl)methyl]-1H-indazol-3-amine

HRID 512943

반응식

HRID 512943 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([F:18])[CH:17]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9](F)=[C:10]([CH:13]=1)[C:11]#[N:12].O.[NH2:20][NH2:21]>C(O)CCC.O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([F:18])[CH:17]=1)[CH2:5][C:6]1[CH:13]=[C:10]2[C:9](=[CH:8][CH:7]=1)[NH:21][N:20]=[C:11]2[NH2:12]

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 441342595-(3,5-Difluorobenzyl)-2-fluorobenzonitrile

생성물 1

HCID 441342655-[(3,5-difluorophenyl)methyl]-1H-indazol-3-amine수율 62%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 22728543Water ethylacetate용매

반응 조건

온도
120 °C

실험 절차

A mixture of 5-(3,5-difluoro-benzyl)-2-fluoro-benzonitrile (20 g, 80.9 mmol) and hydrazine hydrate (19.6 mL, 404 mmol) in n-butanol (200 mL) was heated at 120° C. overnight. The reaction mixture was diluted with water/ethyl acetate and the organic phase washed twice with brine, dried and evaporated. Crude was triturated with diethyl ether and filtered to afford 13 gr of final product. Purification of the resulting organic phase by chromatography over silica gel (DCM/EtOH 95:5) afforded further 6.3 g of the title compound (total amount 19.2 g, 92% yield).

후처리

  1. washthe organic phase washed twice with brine
  2. customdried
  3. customevaporated
  4. customCrude was triturated with diethyl ether
  5. filtrationfiltered

출처 및 근거

ORD 기록
ord-345107f74a5f444b992ecd0eee90b56b
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102662B2

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