methyl 6-(2-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)oxazol-5-yl)picolinate

Base Information

Chemical Name:methyl 6-(2-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)oxazol-5-yl)picolinate
CAS No.:1289563-22-9
Molecular Formula:C₃₃H₃₈N₂O₅Si
Molecular Weight:570.761
Hs Code.:

Synonyms:methyl 6-(2-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)oxazol-5-yl)picolinate

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Chemical Property of methyl 6-(2-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)oxazol-5-yl)picolinate

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Technology Process of methyl 6-(2-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)oxazol-5-yl)picolinate

There total 12 articles about methyl 6-(2-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)oxazol-5-yl)picolinate 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: 73.0%

: 26218-75-7
methyl 6-Bromopicolinate

: 1289563-05-8
2-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)-5-(tributylstannyl)oxazole

: 1289563-22-9
methyl 6-(2-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)oxazol-5-yl)picolinate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; for 16h; Reflux; Inert atmosphere;
DOI:10.1021/jm101597x

Reference yield:

: 1289563-01-4
oxazol-2-yl(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol

: 1289563-22-9
methyl 6-(2-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)oxazol-5-yl)picolinate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C

2.2: 0.08 h

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 16 h / Reflux; Inert atmosphere

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; 3.1: Stille coupling;
DOI:10.1021/jm101597x

Reference yield:

: 1289562-99-7
6-phenoxy-1,2,3,4-tetrahydronaphthalene-2-carboxaldehyde

: 1289563-22-9
methyl 6-(2-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)oxazol-5-yl)picolinate

Guidance literature:: Multi-step reaction with 4 steps

1.1: borane-THF / tetrahydrofuran / 1 h / 20 °C

1.2: 0.67 h / -78 °C

1.3: 2 h / -78 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C

3.2: 0.08 h

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 16 h / Reflux; Inert atmosphere

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; borane-THF; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; 4.1: Stille coupling;
DOI:10.1021/jm101597x