N-[(4-Hydroxymethyl-oxazol-5-yl)-(2-methoxy-pyridin-4-yl)-methyl]-N-(2-vinyl-phenyl)-formamide

Base Information

• Chemical Name: N-[(4-Hydroxymethyl-oxazol-5-yl)-(2-methoxy-pyridin-4-yl)-methyl]-N-(2-vinyl-phenyl)-formamide
• CAS No.: 123148-75-4
• Molecular Formula: C₂₀H₁₉N₃O₄
• Molecular Weight: 365.389
• Mol file: 123148-75-4.mol

Synonyms:

Chemical Property of N-[(4-Hydroxymethyl-oxazol-5-yl)-(2-methoxy-pyridin-4-yl)-methyl]-N-(2-vinyl-phenyl)-formamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(4-Hydroxymethyl-oxazol-5-yl)-(2-methoxy-pyridin-4-yl)-methyl]-N-(2-vinyl-phenyl)-formamide

There total 15 articles about N-[(4-Hydroxymethyl-oxazol-5-yl)-(2-methoxy-pyridin-4-yl)-methyl]-N-(2-vinyl-phenyl)-formamide 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: 82.0%

{5-[(2-Methoxy-pyridin-4-yl)-(2-vinyl-phenylamino)-methyl]-oxazol-4-yl}-methanol (123148-74-3) + formyl acetic anhydride (2258-42-6) → N-[(4-Hydroxymethyl-oxazol-5-yl)-(2-methoxy-pyridin-4-yl)-methyl]-N-(2-vinyl-phenyl)-formamide (123148-75-4)

Guidance literature:

In tetrahydrofuran; for 15h; Ambient temperature;

DOI:10.1021/jo00284a035

Reference yield:

methyl 2-methoxyisonicotinate (26156-51-4) → N-[(4-Hydroxymethyl-oxazol-5-yl)-(2-methoxy-pyridin-4-yl)-methyl]-N-(2-vinyl-phenyl)-formamide (123148-75-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 80 percent / NaBH₄, CaCl₂ / tetrahydrofuran / 12 h / Ambient temperature

2: 94 percent / CrO₃, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 77 percent / methanol / 2.5 h / Heating

4: 100 percent / NaNO₂, Ac₂O/AcOH / 1) a) 0 deg C, 12 h, b) RT, 30 min

5: 95 percent / Na₂CO₃ / CCl₄ / 16 h / Heating

6: NaOMe / methanol / 0.17 h / 0 °C

7: 95 percent / CrO₃, pyridine / CH₂Cl₂ / 0.67 h / Ambient temperature

8: 1.) p-TsOH*H₂O, 2.) NaCNBH₃, AcOH / 1.) toluene, 90 deg C, 2 h, 2.) MeOH, from 0 deg C to RT, 1 h

9: 78 percent / toluene / 1.) 0 deg C, 30 min, 2.) from 0 deg C to RT, 30 min

10: 73 percent / Cu₂O, Et₃N / tetrahydrofuran / 1 h / Ambient temperature

11: 82 percent / NaBH₄, CaCl₂ / tetrahydrofuran; methanol / 21.5 h / Ambient temperature

12: 82 percent / tetrahydrofuran / 15 h / Ambient temperature

With pyridine; chromium(VI) oxide; copper(I) oxide; sodium tetrahydroborate; sodium methylate; acetic anhydride; sodium cyanoborohydride; sodium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; calcium chloride; sodium nitrite; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; toluene;

DOI:10.1021/jo00284a035

Reference yield:

2-nitro-benzeneethanol (15121-84-3) → N-[(4-Hydroxymethyl-oxazol-5-yl)-(2-methoxy-pyridin-4-yl)-methyl]-N-(2-vinyl-phenyl)-formamide (123148-75-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 83 percent / MsCl, DBU / tetrahydrofuran / 12 h / Ambient temperature

2: 60 percent / Fe (powder), acetic acid / ethanol / 1 h / Heating

3: 1.) p-TsOH*H₂O, 2.) NaCNBH₃, AcOH / 1.) toluene, 90 deg C, 2 h, 2.) MeOH, from 0 deg C to RT, 1 h

4: 78 percent / toluene / 1.) 0 deg C, 30 min, 2.) from 0 deg C to RT, 30 min

5: 73 percent / Cu₂O, Et₃N / tetrahydrofuran / 1 h / Ambient temperature

6: 82 percent / NaBH₄, CaCl₂ / tetrahydrofuran; methanol / 21.5 h / Ambient temperature

7: 82 percent / tetrahydrofuran / 15 h / Ambient temperature

With copper(I) oxide; sodium tetrahydroborate; iron; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; calcium chloride; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1021/jo00284a035

upstream raw materials:

{5-[(2-Methoxy-pyridin-4-yl)-(2-vinyl-phenylamino)-methyl]-oxazol-4-yl}-methanol

formyl acetic anhydride

methyl 2-methoxyisonicotinate

2-nitro-benzeneethanol

Refernces