1-((2-(triMethylsilyl)ethoxy)Methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one synthesis
- Product Name:1-((2-(triMethylsilyl)ethoxy)Methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one
- CAS Number:879132-48-6
- Molecular formula:C13H20N2O2Si
- Molecular Weight:264.4
![1,3-DIHYDRO-2H-PYRROLO[2,3-B]PYRIDINE-2-ONE](/CAS/GIF/5654-97-7.gif)
5654-97-7
126 suppliers
$38.00/1g
76513-69-4
363 suppliers
$6.00/1g
879132-48-6
73 suppliers
$13.00/100mg
Yield: 2.26 g
Reaction Conditions:
Stage #1:7-azaoxindole with sodium hydride in tetrahydrofuran;N,N-dimethyl-formamide;mineral oil at 0; for 1 h;Inert atmosphere;
Stage #2:(2-trimethylethylsilylethoxy)methyl chloride in tetrahydrofuran;N,N-dimethyl-formamide;mineral oil at 20; for 21 h;Inert atmosphere;
Steps:
GW-23.1
To a solution of 1H-pyrrolo[2,3-b]pyridin-2(3H)-one (2.00 g, 14.9 mmol) in DMF (30 mL) and THF (30 mL) under nitrogen at 0 °C was added sodium hydride, 60% in mineral oil (0.600 g, 15.0 mmol). The reaction mixture was stirred at 0 °C for 1 h. Then (2- (chloromethoxy)ethyl)trimethylsilane (3.17 mL, 17.9 mmol) was added dropwise over 3 min and the reaction was allowed to warm up to rt without removing the cold bath over 21 h. The reaction mixture was partitioned between water (50 mL) and EtOAc (50 mL), the aqueous was extracted with EtOAc (2 x 50 mL), the combined organic component was washed with water (2 x 50 mL), brine (50 mL), dried over MgS04, filtered, concentrated and purified with a Biotage Horizon (25% EtOAc/hexanes) to afford the title compound (2.26 g ) as viscous orange oil. LC-MS retention time = 3.49 min; m/z = 265.20 [M+H]+. (Column: Phenomenex C18 50 x 2.0 mm 3 μιη. Solvent A = 90% Water : 10% MeOH : 0.1% TFA. Solvent B = 10% Water : 90% MeOH : 0.1% TFA. Flow Rate = 0.8 mL/min. Start % B = 0. Final % B = 100. Gradient Time = 4 minutes, then a l-minute hold at l00% B. Oven temperature = 40 °C. Wavelength = 220 nm). 1H NMR (400 MHZ, DMSO-d6) δ 8.15 (d, J=5.0 Hz, 1H), 7.65 (d, J=7.3 Hz, 1H), 7.05 (dd, J=7.2, 5.4 Hz, 1H), 5.07 (s, 2H), 3.69 (s, 2H), 3.59 (t, J=8.0 Hz, 2H), 0.85 (t, J=8.0 Hz, 2H), -0.06 (s, 9H).
References:
BRISTOL-MYERS SQUIBB COMPANY;BENDER, John A.;GENTLES, Robert G.;PENDRI, Annapurna;WANG, Alan Xiangdong;MEANWELL, Nicholas A.;BENO, Brett R.;FRIDELL, Robert A.;BELEMA, Makonen;NGUYEN, Van N.;YANG, Zhong;WANG, Gan;KUMARAVEL, Selvakumar;THANGATHIRUPATHY, Srinivasan;BORA, Rajesh Onkardas;HOLEHATTI, Shilpa Maheshwarappa;METTU, Mallikarjuna Rao;PANDA, Manoranjan WO2016/172424, 2016, A1 Location in patent:Page/Page column 90; 91
![3,3-dibroMo-1-((2-(triMethylsilyl)ethoxy)Methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one](/CAS/GIF/879132-47-5.gif)
879132-47-5
17 suppliers
$557.00/1g
879132-48-6
73 suppliers
$13.00/100mg
![1-((2-(triMethylsilyl)ethoxy)Methyl)-1H-pyrrolo[2,3-b]pyridine](/CAS/GIF/879132-46-4.gif)
879132-46-4
35 suppliers
$55.00/1g
879132-48-6
73 suppliers
$13.00/100mg
76513-69-4
363 suppliers
$6.00/1g
879132-48-6
73 suppliers
$13.00/100mg
271-63-6
580 suppliers
$9.00/5g
879132-48-6
73 suppliers
$13.00/100mg