phenyl 3-(benzyloxy)-2-bromo-6-[(t-butoxycarbonyl)-amino]-5-methylisonicotinate

Base Information

Chemical Name:phenyl 3-(benzyloxy)-2-bromo-6-[(t-butoxycarbonyl)-amino]-5-methylisonicotinate
CAS No.:1254367-66-2
Molecular Formula:C₂₅H₂₅BrN₂O₅
Molecular Weight:513.388
Hs Code.:

Synonyms:phenyl 3-(benzyloxy)-2-bromo-6-[(t-butoxycarbonyl)-amino]-5-methylisonicotinate

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Chemical Property of phenyl 3-(benzyloxy)-2-bromo-6-[(t-butoxycarbonyl)-amino]-5-methylisonicotinate

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Technology Process of phenyl 3-(benzyloxy)-2-bromo-6-[(t-butoxycarbonyl)-amino]-5-methylisonicotinate

There total 10 articles about phenyl 3-(benzyloxy)-2-bromo-6-[(t-butoxycarbonyl)-amino]-5-methylisonicotinate 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:

: 4248-19-5
tert-butyl carbazate

: 1254367-40-2
phenyl 3-(benzyloxy)-2,6-dibromo-5-methylisonicotinate

: 1254367-67-3
C₂₅H₂₅BrN₂O₅

: 1254367-66-2
phenyl 3-(benzyloxy)-2-bromo-6-[(t-butoxycarbonyl)-amino]-5-methylisonicotinate

Guidance literature:: With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; at 80 ℃; for 3h;

Reference yield:

: 1254367-44-6
C₂₀H₁₆BrNO₄

: 1254367-67-3
C₂₅H₂₅BrN₂O₅

: 1254367-66-2
phenyl 3-(benzyloxy)-2-bromo-6-[(t-butoxycarbonyl)-amino]-5-methylisonicotinate

Guidance literature:: Multi-step reaction with 2 steps

1: phosphorus(V) oxybromide / toluene / 0.75 h / 100 °C

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; phosphorus(V) oxybromide; In 1,4-dioxane; toluene;
DOI:10.1021/jm1015389

Reference yield:

: 1253799-61-9
3-(benzyloxy)-5-chloroisonicotinic acid

: 1254367-67-3
C₂₅H₂₅BrN₂O₅

: 1254367-66-2
phenyl 3-(benzyloxy)-2-bromo-6-[(t-butoxycarbonyl)-amino]-5-methylisonicotinate

Guidance literature:: Multi-step reaction with 8 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane

2: dmap; triethylamine / dichloromethane / 1 h

3: (bis(tricyclohexyl)phosphine)palladium(II) dichloride; anhydrous dipotassium phosphate / water; toluene / 16 h / 100 °C

4: dihydrogen peroxide / water; acetic acid / 6 h / 80 °C

5: phosphorus(V) oxybromide / toluene / 0.5 h / 80 °C

6: dihydrogen peroxide / water; acetic acid / 80 °C

7: phosphorus(V) oxybromide / toluene / 0.75 h / 100 °C

8: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere

With dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (bis(tricyclohexyl)phosphine)palladium(II) dichloride; anhydrous dipotassium phosphate; oxalyl dichloride; dihydrogen peroxide; caesium carbonate; triethylamine; N,N-dimethyl-formamide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; phosphorus(V) oxybromide; In 1,4-dioxane; dichloromethane; water; acetic acid; toluene; 3: Suzuki coupling;
DOI:10.1021/jm1015389