6-(difluoromethyl)-1-(tetrahydro-2H-pyran-2-yl)-5-(2-(trifluoromethyl)phenyl)-1H-indazole

Base Information

Chemical Name:6-(difluoromethyl)-1-(tetrahydro-2H-pyran-2-yl)-5-(2-(trifluoromethyl)phenyl)-1H-indazole
CAS No.:1613505-23-9
Molecular Formula:C₂₀H₁₇F₅N₂O
Molecular Weight:396.36
Hs Code.:

Synonyms:6-(difluoromethyl)-1-(tetrahydro-2H-pyran-2-yl)-5-(2-(trifluoromethyl)phenyl)-1H-indazole

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Chemical Property of 6-(difluoromethyl)-1-(tetrahydro-2H-pyran-2-yl)-5-(2-(trifluoromethyl)phenyl)-1H-indazole

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Technology Process of 6-(difluoromethyl)-1-(tetrahydro-2H-pyran-2-yl)-5-(2-(trifluoromethyl)phenyl)-1H-indazole

There total 6 articles about 6-(difluoromethyl)-1-(tetrahydro-2H-pyran-2-yl)-5-(2-(trifluoromethyl)phenyl)-1H-indazole 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: 45.0%

: 1613505-22-8
1-(tetrahydro-2H-pyran-2-yl)-5-(2-(trifluoromethyl)phenyl)-1H-indazole-6-carbaldehyde

: 1613505-23-9
6-(difluoromethyl)-1-(tetrahydro-2H-pyran-2-yl)-5-(2-(trifluoromethyl)phenyl)-1H-indazole

Guidance literature:: With diethylamino-sulfur trifluoride; In dichloromethane; Reflux;
DOI:10.1021/jm401986p

Reference yield:

: 474330-54-6
5-amino-2-bromo-4-methylbenzoic acid methyl ester

: 1613505-23-9
6-(difluoromethyl)-1-(tetrahydro-2H-pyran-2-yl)-5-(2-(trifluoromethyl)phenyl)-1H-indazole

Guidance literature:: Multi-step reaction with 6 steps

1.1: boron trifluoride diethyl etherate; tert.-butylnitrite / dichloromethane / -78 - 20 °C / Inert atmosphere

1.2: 20 °C

2.1: toluene-4-sulfonic acid / chloroform / 20 - 50 °C

3.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 120 °C / Microwave irradiation

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

5.1: manganese(IV) oxide / dichloromethane / 72 h / 20 °C

6.1: diethylamino-sulfur trifluoride / dichloromethane / Reflux

With manganese(IV) oxide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; diethylamino-sulfur trifluoride; boron trifluoride diethyl etherate; caesium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; water; 3.1: |Suzuki Coupling;
DOI:10.1021/jm401986p

Reference yield:

: 18595-18-1
3-amino-4-methyl benzoic acid methyl ester

: 1613505-23-9
6-(difluoromethyl)-1-(tetrahydro-2H-pyran-2-yl)-5-(2-(trifluoromethyl)phenyl)-1H-indazole

Guidance literature:: Multi-step reaction with 7 steps

1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C / Cooling with ice

2.1: boron trifluoride diethyl etherate; tert.-butylnitrite / dichloromethane / -78 - 20 °C / Inert atmosphere

2.2: 20 °C

3.1: toluene-4-sulfonic acid / chloroform / 20 - 50 °C

4.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 120 °C / Microwave irradiation

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

6.1: manganese(IV) oxide / dichloromethane / 72 h / 20 °C

7.1: diethylamino-sulfur trifluoride / dichloromethane / Reflux

With manganese(IV) oxide; N-Bromosuccinimide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; diethylamino-sulfur trifluoride; boron trifluoride diethyl etherate; caesium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; 4.1: |Suzuki Coupling;
DOI:10.1021/jm401986p