3-b]pyridine synthesis
- Product Name:3-b]pyridine
- CAS Number:1357945-27-7
- Molecular formula:C6H3ClIN3
- Molecular Weight:279.47
![5-Chloro-1H-pyrazolo[4,3-b]pyridine](/CAS/GIF/94220-45-8.gif)
94220-45-8
1357945-27-7
To a solution of 5-chloro-1H-pyrazolo[4,3-b]pyridine (XIII) (13 g, 84.7 mmol) in N,N-dimethylformamide (DMF) (100 mL) was added iodine (43.0 g, 169 mmol), followed by batchwise addition of potassium hydroxide powder (23.75 g, 423 mmol), and the reaction mixture was cooled in an ice water bath. The reaction mixture was stirred at 25 °C overnight. The solid potassium hydroxide was removed by filtration and the filter cake was washed with ethyl acetate (EtOAc). Most of the DMF was evaporated under reduced pressure and the residue was diluted with water (200 mL) and extracted with ethyl acetate (5 × 200 mL). The organic phases were combined, washed with saturated saline (500 mL) and dried over anhydrous sodium sulfate (Na2SO4). The organic phases were concentrated to afford 5-chloro-3-iodo-1H-pyrazolo[4,3-b]pyridine (XIV) as an orange solid (23.5 g, 84.1 mmol, 99.3% yield). The m/z of C6H3ClIN3 was measured to be 279.9 ([M+H]+) by electrospray ionization mass spectrometry (ESIMS).
94220-45-8
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1357945-27-7
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$80.00/250mg
Yield: 99.3%
Reaction Conditions:
with iodine;potassium hydroxide in N,N-dimethyl-formamide at 25;Cooling with ice;
Steps:
1
To a solution of 5-chloro-1H-pyrazolo[4,3-bjpyridine (XIII) (13 g, 84.7 mmol) in DMF (100 mL) was added iodine (43.0 g, 169 mmol) followed by potassium hydroxide powder (23.75 g, 423 mmol) portion wise under ice water cooling. The reaction mixture was stirred at 25°C overnight. The solid KOH was filtered off, washed with EtOAc, most of the DMF was removed under vacuum and the residue was diluted with water (200 mL) and extracted with 5 X 200 mL EtOAc, washed with brine (500 mL), dried over Na2504 and concentrated to give 5- chloro-3-iodo-1H-pyrazolo[4,3-bjpyridine (XIV) as an orange solid (23.5 g, 84.1 mmol, 99.3 % yield). ESIMS found for C6H3C1TN3 mlz 279.9 (M+H).
References:
SAMUMED, LLC.;KC, Sunil Kumar;WALLACE, David Mark;CAO, Jianguo;CHIRUTA, Chandramouli;MARAKOVITS, Joseph Timothy;BOLLU, Venkataiah;HOOD, John WO2017/23989, 2017, A1 Location in patent:Paragraph 0606; 0607
![5-CHLORO-1H-PYRAZOLO[3,4-C]PYRIDINE](/CAS/GIF/76006-08-1.gif)
76006-08-1
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1357945-27-7
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516-12-1
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94220-45-8
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$11.00/250mg
1357945-27-7
66 suppliers
$80.00/250mg
164666-68-6
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1357945-27-7
66 suppliers
$80.00/250mg