methyl 2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-carboxylate 1',1'-dioxide

Base Information

• Chemical Name: methyl 2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-carboxylate 1',1'-dioxide
• CAS No.: 1448039-18-6
• Molecular Formula: C₂₃H₂₄FNO₆S₂
• Molecular Weight: 493.577
• Mol file: 1448039-18-6.mol

Synonyms:methyl 2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-carboxylate 1',1'-dioxide

Chemical Property of methyl 2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-carboxylate 1',1'-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-carboxylate 1',1'-dioxide

There total 5 articles about methyl 2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-carboxylate 1',1'-dioxide 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: 82.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 5-bromo-2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran] 1',1'-dioxide (1448039-05-1) → methyl 2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-carboxylate 1',1'-dioxide (1448039-18-6)

Guidance literature:

With trans-bis(triphenylphosphine)palladium dichloride; triethylamine; In dimethyl sulfoxide; at 100 ℃; for 22h; under 6443.14 - 9150.92 Torr; Inert atmosphere; Autoclave;

Reference yield:

5-bromo-2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran] (1448038-91-2) → methyl 2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-carboxylate 1',1'-dioxide (1448039-18-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic anhydride; urea hydrogen peroxide adduct / acetonitrile / 20 °C

2: triethylamine; trans-bis(triphenylphosphine)palladium dichloride / dimethyl sulfoxide / 22 h / 100 °C / 6443.14 - 9150.92 Torr / Inert atmosphere; Autoclave

With trans-bis(triphenylphosphine)palladium dichloride; urea hydrogen peroxide adduct; triethylamine; trifluoroacetic anhydride; In dimethyl sulfoxide; acetonitrile;

Reference yield:

4-thianylcarbaldehyde (50675-19-9) → methyl 2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-carboxylate 1',1'-dioxide (1448039-18-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trifluoroacetic acid / chloroform / 18 h / 0 - 50 °C

2.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.08 h / 0 °C

2.2: 3 h / 5 - 20 °C

3.1: triethylamine / 1,2-dichloro-ethane / 42 h / 80 °C

4.1: trifluoroacetic anhydride; urea hydrogen peroxide adduct / acetonitrile / 20 °C

5.1: triethylamine; trans-bis(triphenylphosphine)palladium dichloride / dimethyl sulfoxide / 22 h / 100 °C / 6443.14 - 9150.92 Torr / Inert atmosphere; Autoclave

With trans-bis(triphenylphosphine)palladium dichloride; boron trifluoride diethyl etherate; urea hydrogen peroxide adduct; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; In tetrahydrofuran; chloroform; dimethyl sulfoxide; 1,2-dichloro-ethane; acetonitrile; 1.1: |Fischer Indole Synthesis;

upstream raw materials:

5-bromo-2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]

methanol

carbon monoxide

5-bromo-2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran] 1',1'-dioxide

Downstream raw materials:

rac-N-[(3-chloropyridin-2-yl)methyl]-2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-carboxamide 1',1'-dioxide

2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-N-{[(5-trifluoromethyl)pyridin-2-yl]methyl}-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-carboxamide 1',1'-dioxide

2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-carboxylic acid 1',1'-dioxide