1-(4-fluorobenzyl)-1H-indole-2,3-dione synthesis
- Product Name:1-(4-fluorobenzyl)-1H-indole-2,3-dione
- CAS Number:313245-18-0
- Molecular formula:C15H10FNO2
- Molecular Weight:255.24
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459-46-1
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313245-18-0
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Yield:313245-18-0 82%
Reaction Conditions:
Stage #1: indole-2,3-dionewith sodium hydride in N,N-dimethyl-formamide at 0; for 1 h;
Stage #2: 4-Fluorobenzyl bromide in N,N-dimethyl-formamide at 20; for 3 h;
Steps:
3
Intermediate-3 : 1 -(4-Fluorobenzyl)indoline-2,3-dione:To a stirred solution of isatin (10 g, 67 mmol) in dry DMF (100 ml) at 0 °C was added NaH (2.1 g, 87.5 mmol) step wise. The solution was stirred for lh at 0 °C. The /7-fluorobenzyl bromide (11 mL, 81.1 mmol) was added dropwise. The course of reaction was monitored with TLC. After addition the reaction was stirred at room temperature for 3 h. The reaction mixture was quenched with addition of ice water, the phases were separated. The reaction mixture was extracted with EtOAc (2 x 250 ml). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography, with an isocratic elution of 40% ethyl acetate in petroleum ether to afford the title compound (14 g, 82%) as an off white solid. MS (ES+) m/z: 256.1 (M+l).
References:
WO2012/49555,2012,A1 Location in patent:Page/Page column 47
91-56-5
436 suppliers
$5.00/25g
352-11-4
379 suppliers
$5.00/25g
313245-18-0
14 suppliers
$120.00/0.500g
91-56-5
436 suppliers
$5.00/25g
313245-18-0
14 suppliers
$120.00/0.500g