Methanol → 3-Pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-6-ylamine

HRID 1827478노트

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HRID 1827478 반응식
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[N:9][N:10]2[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][CH:5]=1)([O-])=O.Cl[Sn]Cl.O.CO>CCOC(C)=O.[OH-].[Na+]>[N:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]#[C:21][C:8]1[C:7]2[C:11](=[CH:12][C:4]([NH2:1])=[CH:5][CH:6]=2)[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:19])([CH3:18])[CH3:20])[N:9]=1

참가 물질

7

반응물 4

HCID 887Methanol2회HCID 962WaterHCID 24479Stannous ChlorideHCID 235778736-Nitro-3-pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

생성물 1

HCID 235778473-Pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-6-ylamine

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매2회HCID 14798Sodium Hydroxide용매

실험 절차

A mixture of 6-Nitro-3-pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (2 mmol), SnCl2 (1.37 g, 6.0 mmol), water (0.5 mL), and MeOH (10 mL), were stirred in a 60 deg C oil bath for 30 min at which time HPLC indicated complete reduction. The resulting mixture was stripped of methanol, suspended in EtOAc (50 mL) and diluted with 1M NaOH (18 mL). The resulting emulsion was gently extracted EtOAc (10×25 ml). The combined organics were extracted with 1M Na2CO3, brine, dried over MgSO4, concentrated and filtered through a pad of silica eluted with EtOAc. The yield of crude product for two steps was 701 mg, 96% mass recovery. ESIMS (M+H+): 365.1.

후처리

  1. extractionThe combined organics were extracted with 1M Na2CO3, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. filtrationfiltered through a pad of silica
  5. washeluted with EtOAc

출처 및 근거

ORD 기록
ord-d76a9f4a161d42ed990a840dc60e8e52
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053107B2

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