4-tert-butyl-2-(2-(4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine]-1-yl)phenylamino)thiazole-5-carbonitrile

Base Information

• Chemical Name: 4-tert-butyl-2-(2-(4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine]-1-yl)phenylamino)thiazole-5-carbonitrile
• CAS No.: 1554015-93-8
• Molecular Formula: C₃₂H₄₀ClN₅OS
• Molecular Weight: 578.221
• Mol file: 1554015-93-8.mol

Synonyms:4-tert-butyl-2-(2-(4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine]-1-yl)phenylamino)thiazole-5-carbonitrile

Chemical Property of 4-tert-butyl-2-(2-(4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine]-1-yl)phenylamino)thiazole-5-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-tert-butyl-2-(2-(4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine]-1-yl)phenylamino)thiazole-5-carbonitrile

There total 11 articles about 4-tert-butyl-2-(2-(4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine]-1-yl)phenylamino)thiazole-5-carbonitrile 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: 44.0%

1-(2-bromophenyl)-4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine] (1554015-91-6) + 2-amino-4-(tert-butyl)thiazole-5-carbonitrile (303994-99-2) → 4-tert-butyl-2-(2-(4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine]-1-yl)phenylamino)thiazole-5-carbonitrile (1554015-93-8)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 110 ℃; for 18h; Inert atmosphere;

Reference yield:

pivaloyl chloride (3282-30-2) → 4-tert-butyl-2-(2-(4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine]-1-yl)phenylamino)thiazole-5-carbonitrile (1554015-93-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / 1,2-dichloro-ethane / 4 h / 23 °C

2.1: Dess-Martin periodane / 0 - 20 °C / Inert atmosphere

3.1: hydrogenchloride / dichloromethane; water; 1,4-dioxane / 1 h / 0 °C

3.2: 1.5 h / 0 °C

4.1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane / 16 h / -78 - 20 °C

5.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 18 h / 110 °C / Microwave irradiation; Inert atmosphere

6.1: sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 18 h / 110 °C / Inert atmosphere

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate; caesium carbonate; Dess-Martin periodane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; dichloromethane; water; 1,2-dichloro-ethane; toluene;

Reference yield:

4-carbethoxypiperidine (1126-09-6) → 4-tert-butyl-2-(2-(4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine]-1-yl)phenylamino)thiazole-5-carbonitrile (1554015-93-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate; ethanol / tetrahydrofuran / 0 - 20 °C

3.1: Dess-Martin periodane / 0 - 20 °C / Inert atmosphere

4.1: hydrogenchloride / dichloromethane; water; 1,4-dioxane / 1 h / 0 °C

4.2: 1.5 h / 0 °C

5.1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane / 16 h / -78 - 20 °C

6.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 18 h / 110 °C / Microwave irradiation; Inert atmosphere

7.1: sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 18 h / 110 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; ethanol; sodium carbonate; caesium carbonate; Dess-Martin periodane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;

upstream raw materials:

4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine]

1-(2-bromophenyl)-4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine]

2-amino-4-(tert-butyl)thiazole-5-carbonitrile

(1-tert-butoxycarbonylpiperidine-4-)-carbaldehyde

Downstream raw materials:

4-tert-butyl-2-({2-[4-chloro-1'-neopentyl-7-hydroxy-1,2-dihydrospiro[indole-3,4'-piperidine]-1-yl]phenyl}amino)-1,3-thiazole-5-carbonitrile