{5-[4-(3-formyl-2-methoxy-3-phenyl-2,3-dihydro-benzofuran-7-yl)-1-methyl-1H-indol-3-yl]-oxazol-2-ylmethyl}-phosphonic acid dimethyl ester

Base Information

• Chemical Name: {5-[4-(3-formyl-2-methoxy-3-phenyl-2,3-dihydro-benzofuran-7-yl)-1-methyl-1H-indol-3-yl]-oxazol-2-ylmethyl}-phosphonic acid dimethyl ester
• CAS No.: 321527-27-9
• Molecular Formula: C₃₁H₂₉N₂O₇P
• Molecular Weight: 572.554

Synonyms:{5-[4-(3-formyl-2-methoxy-3-phenyl-2,3-dihydro-benzofuran-7-yl)-1-methyl-1H-indol-3-yl]-oxazol-2-ylmethyl}-phosphonic acid dimethyl ester

Chemical Property of {5-[4-(3-formyl-2-methoxy-3-phenyl-2,3-dihydro-benzofuran-7-yl)-1-methyl-1H-indol-3-yl]-oxazol-2-ylmethyl}-phosphonic acid dimethyl ester

Chemical Property:

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Technology Process of {5-[4-(3-formyl-2-methoxy-3-phenyl-2,3-dihydro-benzofuran-7-yl)-1-methyl-1H-indol-3-yl]-oxazol-2-ylmethyl}-phosphonic acid dimethyl ester

There total 27 articles about {5-[4-(3-formyl-2-methoxy-3-phenyl-2,3-dihydro-benzofuran-7-yl)-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:

{5-[4-(3-hydroxymethyl-2-methoxy-3-phenyl-2,3-dihydro-benzofuran-7-yl)-1-methyl-1H-indol-3-yl]-oxazol-2-ylmethyl}-phosphonic acid dimethyl ester → {5-[4-(3-formyl-2-methoxy-3-phenyl-2,3-dihydro-benzofuran-7-yl)-1-methyl-1H-indol-3-yl]-oxazol-2-ylmethyl}-phosphonic acid dimethyl ester (321527-27-9)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 25 ℃; for 8h;

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

Reference yield:

4-bromo-1H-indole (52488-36-5) → {5-[4-(3-formyl-2-methoxy-3-phenyl-2,3-dihydro-benzofuran-7-yl)-1-methyl-1H-indol-3-yl]-oxazol-2-ylmethyl}-phosphonic acid dimethyl ester (321527-27-9)

Guidance literature:

Multi-step reaction with 13 steps

1: TFA / 0.5 h / 25 °C

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

3: 79 percent / EDC; HOBt / CH₂Cl₂ / 2 h / 25 °C

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

5: 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide / tetrahydrofuran; dimethylsulfoxide / 3 h / 25 °C

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

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

8: 92 percent / TBAF / tetrahydrofuran / 0.25 h / 25 °C

9: 94 percent / I₂; Ph₃P; imidazole / CH₂Cl₂ / 0.17 h / 0 °C

10: 86 percent / KHMDS / tetrahydrofuran; toluene / 0.17 h / 0 °C

11: 60 percent / K₂CO₃ / [Pd(dppf)Cl₂]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 2 h / 85 °C

12: aq. HF / acetonitrile / 0.25 h / 0 °C

13: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 8 h / 25 °C

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; hexachloroethane; hydrogen fluoride; tetrabutyl ammonium fluoride; water; iodine; tetra(n-butyl)ammonium hydrogensulfate; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; trifluoroacetic acid; 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; acetonitrile; benzene; 6: Gabriel-Robinson cyclodehydration / 11: Suzuki reaction;

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

Reference yield:

phenylmagnesium bromide → {5-[4-(3-formyl-2-methoxy-3-phenyl-2,3-dihydro-benzofuran-7-yl)-1-methyl-1H-indol-3-yl]-oxazol-2-ylmethyl}-phosphonic acid dimethyl ester (321527-27-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 100 percent / tetrahydrofuran / 2 h / -78 - 25 °C

2.1: 93 percent / 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide / tetrahydrofuran; dimethylsulfoxide / 1 h / 25 °C

3.1: 86 percent / nBuLi / hexane; tetrahydrofuran / 12 h / 0 °C

4.1: 100 percent / aq. HCl / ethanol; CH₂Cl₂ / 12 h / 40 °C

5.1: 75 percent / K₂CO₃ / acetone / 2 h / 56 °C

6.1: 91 percent / mCPBA / CH₂Cl₂ / 6 h / 25 °C

7.1: 54 percent / KOtBu / tetrahydrofuran; dimethylformamide / 0.03 h / -57 °C

8.1: 99 percent / imidazole / dimethylformamide / 12 h / 25 °C

9.1: LiHMDS / tetrahydrofuran / 0.25 h / -78 °C

9.2: O₂ / tetrahydrofuran / 0.25 h / -78 °C

9.3: 94 percent / SnCl₂; aq. HCl / tetrahydrofuran / 0.5 h / -78 - 0 °C

10.1: 92 percent / DIBAL-H / toluene / 1 h / -78 °C

11.1: 91 percent / NaH / tetrahydrofuran / 24 h / 25 °C

12.1: 50 percent / KOAc / [Pd(dppf)Cl₂]*CH₂Cl₂ / dimethylsulfoxide / 4 h / 90 °C

13.1: 60 percent / K₂CO₃ / [Pd(dppf)Cl₂]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 2 h / 85 °C

14.1: aq. HF / acetonitrile / 0.25 h / 0 °C

15.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 8 h / 25 °C

With 1H-imidazole; hydrogenchloride; n-butyllithium; hydrogen fluoride; potassium tert-butylate; potassium acetate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; 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; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 3.1: Wittig reaction / 13.1: Suzuki reaction;

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

upstream raw materials:

4-bromo-1H-indole

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

O-methoxymethyl-3-bromosalicylaldehyde

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

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