1-(3-methyl-2-phenyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran]

Base Information

• Chemical Name: 1-(3-methyl-2-phenyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran]
• CAS No.: 1259513-65-9
• Molecular Formula: C₃₂H₃₃N₃O₂
• Molecular Weight: 491.633
• Mol file: 1259513-65-9.mol

Synonyms:1-(3-methyl-2-phenyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran]

Chemical Property of 1-(3-methyl-2-phenyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3-methyl-2-phenyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran]

There total 5 articles about 1-(3-methyl-2-phenyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran] 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: 37.0%

4-chloro-3-methyl-2-phenylquinoline (64495-56-3) + 6-morpholino-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran] (1259512-05-4) → 1-(3-methyl-2-phenyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran] (1259513-65-9)

Guidance literature:

6-morpholino-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.333333h; Inert atmosphere;

4-chloro-3-methyl-2-phenylquinoline; In N,N-dimethyl-formamide; mineral oil; at 130 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jm300679u

Reference yield:

4-bromo-2-nitro-benzoic acid methyl ester (100487-82-9) → 1-(3-methyl-2-phenyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran] (1259513-65-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / mineral oil; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere

1.2: 19 h / 40 °C / Inert atmosphere

2.1: iron / acetic acid / 2 h / 100 °C / Inert atmosphere

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.83 h / 80 °C / Inert atmosphere

4.1: dmap; pyridine / 0.5 h / 85 °C / Inert atmosphere

5.1: dicyclohexyl(2',4',6'-triisopropylbiphenyl-4-yl)phosphine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / tert-butyl alcohol / 4 h / 110 °C / Inert atmosphere

6.1: hydrogenchloride / acetonitrile; water / 20 - 120 °C / Inert atmosphere

7.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere

7.2: 12 h / 130 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl(2',4',6'-triisopropylbiphenyl-4-yl)phosphine; iron; sodium hydride; caesium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; In water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; tert-butyl alcohol;

DOI:10.1021/jm300679u

Reference yield:

methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate (1202765-53-4) → 1-(3-methyl-2-phenyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran] (1259513-65-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: iron / acetic acid / 2 h / 100 °C / Inert atmosphere

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.83 h / 80 °C / Inert atmosphere

3.1: dmap; pyridine / 0.5 h / 85 °C / Inert atmosphere

4.1: dicyclohexyl(2',4',6'-triisopropylbiphenyl-4-yl)phosphine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / tert-butyl alcohol / 4 h / 110 °C / Inert atmosphere

5.1: hydrogenchloride / acetonitrile; water / 20 - 120 °C / Inert atmosphere

6.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere

6.2: 12 h / 130 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl(2',4',6'-triisopropylbiphenyl-4-yl)phosphine; iron; sodium hydride; caesium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; In water; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; tert-butyl alcohol;

DOI:10.1021/jm300679u

upstream raw materials:

4-chloro-3-methyl-2-phenylquinoline

6-morpholino-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]

4-bromo-2-nitro-benzoic acid methyl ester

methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate