4'-[(R)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid

Base Information

• Chemical Name: 4'-[(R)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid
• CAS No.: 1354808-87-9
• Molecular Formula: C₂₉H₂₆N₂O₃
• Molecular Weight: 450.537

Synonyms:4'-[(R)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid

Chemical Property of 4'-[(R)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 4'-[(R)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid

There total 9 articles about 4'-[(R)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid 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:

4'-[3-[hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester (1354808-49-3) → 4'-[(R)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid (1354808-87-9) + 4'-[(R)-3-[(Z)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid (1354808-88-0) + 4'-[(S)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid (1354808-85-7) + 4'-[(S)-3-[(Z)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid (1354808-86-8)

Guidance literature:

4'-[3-[hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester; With water; lithium hydroxide; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 2h;

With potassium hydrogensulfate; In tetrahydrofuran; methanol; water;

Reference yield:

4-bromo-benzaldehyde (1122-91-4) → 4'-[(R)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid (1354808-87-9)

Guidance literature:

Multi-step reaction with 8 steps

1: morpholine / Reflux

2: 2-methyltetrahydrofuran / 20 °C

3: acetic acid; sulfuric acid / 15 h / 110 °C

4: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / N,N-dimethyl-formamide

5: n-butyllithium / tetrahydrofuran / -100 °C

6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane

7: hydroxylamine hydrochloride; sodium acetate / ethanol; water / Reflux

8: hydrogenchloride

With morpholine; hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; n-butyllithium; sulfuric acid; hydroxylamine hydrochloride; sodium acetate; sodium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; triethylamine; In tetrahydrofuran; 2-methyltetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; 6: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2013.06.017

Reference yield:

ethyl 3-(4-bromophenyl)-2-cyanoacrylate (42205-33-4,18861-58-0) → 4'-[(R)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid (1354808-87-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 2-methyltetrahydrofuran / 20 °C

2: acetic acid; sulfuric acid / 15 h / 110 °C

3: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / N,N-dimethyl-formamide

4: n-butyllithium / tetrahydrofuran / -100 °C

5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane

6: hydroxylamine hydrochloride; sodium acetate / ethanol; water / Reflux

7: hydrogenchloride

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; n-butyllithium; sulfuric acid; hydroxylamine hydrochloride; sodium acetate; sodium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; triethylamine; In tetrahydrofuran; 2-methyltetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; 5: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2013.06.017

upstream raw materials:

4'-[3-[hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester

4-bromo-benzaldehyde

ethyl 3-(4-bromophenyl)-2-cyanoacrylate

ethyl 3-(4-bromophenyl)-2-cyano-3-o-tolylpropanoate

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