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

HRID 1827478ノート

反応式

HRID 1827478 の反応式
[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

参加物

7

反応物 4

HCID 887Methanol2 回HCID 962WaterHCID 24479Stannous ChlorideHCID 235778736-Nitro-3-pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒2 回HCID 14798Sodium Hydroxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d76a9f4a161d42ed990a840dc60e8e52
出典データセット
uspto-grants-2006_05
特許番号
US07053107B2

反応ノート

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