3,3-dibroMo-1-((2-(triMethylsilyl)ethoxy)Methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one synthesis
- Product Name:3,3-dibroMo-1-((2-(triMethylsilyl)ethoxy)Methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one
- CAS Number:879132-47-5
- Molecular formula:C13H18Br2N2O2Si
- Molecular Weight:422.19
![1-((2-(triMethylsilyl)ethoxy)Methyl)-1H-pyrrolo[2,3-b]pyridine](/CAS/GIF/879132-46-4.gif)
879132-46-4
38 suppliers
$55.00/1g
879132-47-5
23 suppliers
$557.00/1g
Yield:879132-47-5 85%
Reaction Conditions:
with pyridinium hydrobromide perbromide in 1,4-dioxane;
Steps:
3,3-Dibromo-1 -((2-(trimethylsilyl)ethoxy)methyl)-1 H-pyrrolo[2,3-b]pyridin-2(3H)-one 2.3
A mechanically-stirred suspension of pyridinium tribromide (646 g, 2.02 mol) in1,4-dioxane (900 ml) was cooled to 10-15 00 using an ice/water bath, and a solution of2.2 (100 g, 403.2 mmol) in 1,4-dioxane (500 ml) was added dropwise (NOTE: nosignificant exotherm is observed, but the reaction is kept cool to minimise formation of polymeric by-products). After stirring for 2 hours at 10-15 00, the mixture was partitioned between water (1.5 L) and ethyl acetate (1.5 L). The ethyl acetate layer was collected, and washed with water (2 x 1 L), saturated aqueous sodium bicarbonate solution (1 L), sodium thiosulfate solution (1M solution, 1 L), and brine (2 x 1 L). The ethyl acetate layerwas dried over magnesium sulfate and evaporated to provide compound 2.3 (144 g, 85% yield). 1H NMR (ODd3, 300 MHz): O -0.03 (5, 9H), 0.97 (dd, 2H), 3.70 (dd, 2H), 5.32 (5, 2H), 7.15 (dd, 1H), 7.87 (dd, 1H), 8.30 (dd, 1H). UPLC-MS (short basic) rt 1.00 (421, 423, 425 [M+H]), 89% pure.
References:
WO2018/211275,2018,A1 Location in patent:Page/Page column 128; 129
271-63-6
580 suppliers
$9.00/5g
879132-47-5
23 suppliers
$557.00/1g
76513-69-4
365 suppliers
$6.00/1g
879132-47-5
23 suppliers
$557.00/1g