[5-(4-{3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-1-phenyl-ethyl]-2-methoxy-phenyl}-1-methyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester

Base Information

• Chemical Name: [5-(4-{3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-1-phenyl-ethyl]-2-methoxy-phenyl}-1-methyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester
• CAS No.: 321529-22-0
• Molecular Formula: C₃₈H₄₉N₂O₇PSi
• Molecular Weight: 704.876

Synonyms:[5-(4-{3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-1-phenyl-ethyl]-2-methoxy-phenyl}-1-methyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester

Chemical Property of [5-(4-{3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-1-phenyl-ethyl]-2-methoxy-phenyl}-1-methyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of [5-(4-{3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-1-phenyl-ethyl]-2-methoxy-phenyl}-1-methyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester

There total 11 articles about [5-(4-{3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-1-phenyl-ethyl]-2-methoxy-phenyl}-1-methyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

[5-(4-bromo-1-methyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester (321527-42-8) + 2-{3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-1-phenyl-ethyl]-2-methoxy-phenyl}-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane → [5-(4-{3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-1-phenyl-ethyl]-2-methoxy-phenyl}-1-methyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester (321529-22-0)

Guidance literature:

With potassium carbonate; [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; In 1,2-dimethoxyethane; at 85 ℃; for 2h;

DOI:10.1002/1521-3773(20001002)39:19<3473::AID-ANIE3473>3.0.CO;2-E

Reference yield:

2-(4-bromo-1H-indol-3-yl)ethan-1-amine (108061-74-1) → [5-(4-{3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-1-phenyl-ethyl]-2-methoxy-phenyl}-1-methyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester (321529-22-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 79 percent / EDC; HOBt / CH₂Cl₂ / 2 h / 25 °C

2: DDQ; H₂O / tetrahydrofuran / 3 h / 0 °C

3: 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide / tetrahydrofuran; dimethylsulfoxide / 3 h / 25 °C

4: Cl₃CCCl₃; Ph₃P; Et₃N / 0.25 h / 25 °C

5: nBu₄NHSO₄; aq. NaOH / benzene / 0.33 h / 25 °C

6: 92 percent / TBAF / tetrahydrofuran / 0.25 h / 25 °C

7: 94 percent / I₂; Ph₃P; imidazole / CH₂Cl₂ / 0.17 h / 0 °C

8: 86 percent / KHMDS / tetrahydrofuran; toluene / 0.17 h / 0 °C

9: 52 percent / K₂CO₃ / [Pd(dppf)Cl₂]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 2 h / 85 °C

With 1H-imidazole; sodium hydroxide; hexachloroethane; tetrabutyl ammonium fluoride; water; iodine; tetra(n-butyl)ammonium hydrogensulfate; potassium hexamethylsilazane; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; toluene; benzene; 4: Gabriel-Robinson cyclodehydration / 9: Suzuki reaction;

DOI:10.1002/1521-3773(20001002)39:19<3473::AID-ANIE3473>3.0.CO;2-E

Reference yield:

4-bromo-3-[(E)-2-nitro-1-ethenyl]-1H-indole (303068-04-4) → [5-(4-{3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-1-phenyl-ethyl]-2-methoxy-phenyl}-1-methyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester (321529-22-0)

Guidance literature:

Multi-step reaction with 10 steps

1: LiAlH₄ / tetrahydrofuran / 4 h / 25 - 65 °C

2: 79 percent / EDC; HOBt / CH₂Cl₂ / 2 h / 25 °C

3: DDQ; H₂O / tetrahydrofuran / 3 h / 0 °C

4: 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide / tetrahydrofuran; dimethylsulfoxide / 3 h / 25 °C

5: Cl₃CCCl₃; Ph₃P; Et₃N / 0.25 h / 25 °C

6: nBu₄NHSO₄; aq. NaOH / benzene / 0.33 h / 25 °C

7: 92 percent / TBAF / tetrahydrofuran / 0.25 h / 25 °C

8: 94 percent / I₂; Ph₃P; imidazole / CH₂Cl₂ / 0.17 h / 0 °C

9: 86 percent / KHMDS / tetrahydrofuran; toluene / 0.17 h / 0 °C

10: 52 percent / K₂CO₃ / [Pd(dppf)Cl₂]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 2 h / 85 °C

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; hexachloroethane; tetrabutyl ammonium fluoride; water; iodine; tetra(n-butyl)ammonium hydrogensulfate; potassium hexamethylsilazane; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; toluene; benzene; 5: Gabriel-Robinson cyclodehydration / 10: Suzuki reaction;

DOI:10.1002/1521-3773(20001002)39:19<3473::AID-ANIE3473>3.0.CO;2-E

upstream raw materials:

[5-(4-bromo-1-methyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester

2-(4-bromo-1H-indol-3-yl)ethan-1-amine

4-bromo-3-[(E)-2-nitro-1-ethenyl]-1H-indole

[5-(4-bromo-1-methyl-1H-indol-3-yl)-oxazol-2-yl]-methanol

Downstream raw materials:

(5-{4-[3-(1-formyl-2-methoxy-1-phenyl-ethyl)-2-methoxy-phenyl]-1-methyl-1H-indol-3-yl}-oxazol-2-ylmethyl)-phosphonic acid dimethyl ester

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