ChemicalBook CAS DataBase List URMC-099

URMC-099 synthesis

11synthesis methods

Product Name:URMC-099
CAS Number:1229582-33-5
Molecular formula:C27H27N5
Molecular Weight:421.54

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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144104-59-6
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1229582-33-5
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Yield: 34%

Reaction Conditions:

Stage #1:3-iodo-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine;1H-indole-5-boronic acid with tetrakis(triphenylphosphine) palladium⁽⁰⁾;sodium carbonate in 1,4-dioxane;water at 70; for 8 h;Inert atmosphere;
Stage #2: with potassium carbonate in methanol;water at 60; for 6 h;

Steps:

Compound 6
General procedure: (i) A mixture of intermediate A5 (300 mg, 0.51 mmol), phenylboronic acid (75 mg, 0.61 mmol), Pd(PPh₃)₄ ( mg, mmol) and Na₂CO₃ (108 mg, 1.02 mmol) in 1,4-Dioxane (8 mL) and H₂O (2 mL) was heated at 70 °C for 8 h under N₂. The solvent was removed and the residue was partitioned between EtOAc and H₂O. The combined organics were collected and dried over anhydrous Na₂SO₄ and concentrated in vacuo. The crude material goes directly to the next step without purification. (ii) To a solution of the crude material and K₂CO₃ (141 mg, 1.02 mmol) in MeOH (8 mL) and H₂O (2 mL) was heated at 60 °C for 6 h. The solvent was removed and the residue was partitioned between EtOAc and H₂O. The combined organics were collected and dried over anhydrous Na₂SO₄. The residue after evaporation was purified on silica gel column (DCM/MeOH = 20/1) to afford compound 6 (86 mg, 44 %) as a white solid.

References:

Yang, Bowen;Wu, Qian;Huan, Xiajuan;Wang, Yingqing;Sun, Yin;Yang, Yueyue;Liu, Tongchao;Wang, Xin;Chen, Lin;Xiong, Bing;Zhao, Dongmei;Miao, Zehong;Chen, Danqi [Bioorganic and Medicinal Chemistry Letters,2021,vol. 33,art. no. 127749] Location in patent:supporting information

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1229582-33-5
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References

109-01-3 Synthesis