Potassium Acetate → (5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methyl acetate

HRID 913839Notes

Reaction equation

HRID 913839 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11]Br)[CH:10]=1)[N:7]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:6]=[CH:5]2.[C:21]([O-:24])(=[O:23])[CH3:22].[K+]>CN(C)C=O.C(OCC)C>[C:21]([O:24][CH2:11][C:9]1[CH:10]=[C:2]([Br:1])[CH:3]=[C:4]2[C:8]=1[N:7]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:6]=[CH:5]2)(=[O:23])[CH3:22]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 575461635-bromo-7-(bromomethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole

Product 1

HCID 57546198(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methyl acetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-7-(bromomethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (940 mg, 2.237 mmol) in dimethylformamide (10 mL) at room temperature was added potassium acetate (659 mg, 6.71 mmol). After 10 min, the reaction was placed in a 40° C. bath and stirred for 1 h. The reaction was cooled to room temperature, diluted with diethyl ether, washed with water (2×), then brine, dried over magnesium sulfate, and concentrated to give 1.04 g (quant.) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 7.95 (s, 1H), 7.86 (d, J=1.8, 1H), 7.55 (d, J=1.2, 1H), 5.81 (s, 2H), 5.52 (s, 2H), 3.49 (m, 2H), 2.08 (s, 3H), 0.84 (m, 2H), −0.09 (s, 9H; 13C NMR (126 MHz, CDCl3) δ ppm 170.2, 137.1, 133.4, 132.2, 128.1, 124.1, 120.9, 114.1, 79.6, 66.3, 63.0, 21.1, 17.8, −1.4.

Workup

  1. customwas placed in a 40° C.
  2. washwashed with water (2×)
  3. dry with materialbrine, dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give 1.04 g (quant.) as a colorless oil

Sources & evidence

ORD record
ord-1a596961e2d5411591e824047d3acdf1
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

Loading…