Sodium Cyanide → 2-(5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)acetonitrile

HRID 913915Notes

Reaction equation

HRID 913915 reaction equation
CS(O[CH2:6][C:7]1[C:15]2[C:11](=[CH:12][N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:14]=2)[CH:10]=[C:9]([Cl:24])[CH:8]=1)(=O)=O.[C-:25]#[N:26].[Na+]>CN(C)C=O.C(OCC)C>[Cl:24][C:9]1[CH:8]=[C:7]([CH2:6][C:25]#[N:26])[C:15]2[C:11](=[CH:12][N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:14]=2)[CH:10]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 57545918(5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methyl methanesulfonate

Product 1

HCID 575459172-(5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methyl methanesulfonate (3.25 g, 8.3 mmol) in dimethylformamide (10 mL) at room temperature was added sodium cyanide (0.815 g, 16.6 mmol). The reaction was placed in a 60° C. oil bath and allowed to stir for 30 min. The reaction was cooled, diluted with diethyl ether, washed with water (2×), then brine, dried over magnesium sulfate, and concentrated to give 2.33 g (87%). 1H-NMR (CDCl3, 500 MHz) δ 8.07 (s, 1H), 7.62 (d, J=1.2 Hz, 1H), 7.32 (d, J=1.2 Hz, 1H), 5.68 (s, 2H), 4.09 (s, 2H), 3.62 (t, J=8.2 Hz, 2H), 0.93 (t, J=7.9 Hz, 2H), -0.04 (s, 9H), 13C NMR (126 MHz, CDCl3) δ ppm 145.7, 127.7, 126.4, 123.2, 122.4, 121.8, 119.5, 117.0, 82.1, 67.9, 19.4, 17.9, −1.4.

Workup

  1. customwas placed in a 60° C.
  2. temperatureThe reaction was cooled
  3. washwashed with water (2×)
  4. dry with materialbrine, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give 2.33 g (87%)

Sources & evidence

ORD record
ord-b1a6f55f69b9466495e0c1c44c7448e2
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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