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ChemicalBook CAS DataBase List tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate
1201187-44-1

tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate synthesis

6synthesis methods
4248-19-5 Synthesis
tert-Butyl carbamate

4248-19-5
384 suppliers
$5.00/5g

1201186-54-0 Synthesis
N-Tosyl-5-bromo-4,7-diazaindole

1201186-54-0
178 suppliers
$41.00/100mg

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Yield:1201187-44-1 75%

Reaction Conditions:

with palladium diacetate;potassium carbonate;4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene in 1,4-dioxane at 105; for 2.5 h;

Steps:

56.3 Step 3: tert-butyl (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate
To a solution of 2-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (624 mg, 1.77 mmol) in1,4-dioxane (10 mL) were added tert-butyl carbamate (311 mg, 2.65 mmol), potassium carbonate(734 mg, 5.31 mmol), xantphos (209 mg, 0.35 mmol) and palladium acetate (41 mg, 0.17 mmol).The mixture was heated to 105 oc and stirred for 2.5 h. The reaction mixture was concentrated invacuo and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 1011)to give the title compound as a white solid (513 mg, 75 %).

References:

SUNSHINE LAKE PHARMA CO., LTD.;TANG, Changhua;REN, Qingyun;YIN, Junjun;YI, Kai;LEI, Yibo;WANG, Yejun;ZHANG, Yingjun WO2018/108125, 2018, A1 Location in patent:Paragraph 00588

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