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

HRID 1827478Notes

Reaction equation

HRID 1827478 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d76a9f4a161d42ed990a840dc60e8e52
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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