Pyridine → methyl 1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate

HRID 1404182Notes

Reaction equation

HRID 1404182 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:7]=[CH:6][NH:5][C:4]=1[C:8]([O:10][CH3:11])=[O:9].[F:14][C:15]([F:29])([C:20]1[CH:24]=[CH:23][NH:22][C:21]=1[C:25]([O:27][CH3:28])=[O:26])[C:16]([F:19])([F:18])[F:17].[Cl:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.N1C=CC=CC=1>ClCCl>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([N:5]2[CH:6]=[CH:7][C:3]([C:2]([F:1])([F:12])[F:13])=[C:4]2[C:8]([O:10][CH3:11])=[O:9])=[CH:33][CH:32]=1.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([N:22]2[CH:23]=[CH:24][C:20]([C:15]([F:14])([F:29])[C:16]([F:19])([F:18])[F:17])=[C:21]2[C:25]([O:27][CH3:28])=[O:26])=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 742994-Chlorophenylboronic acidHCID 90405535methyl 3-(trifluoromethyl)-1H-pyrrole-2-carboxylateHCID 90405804methyl 3-(perfluoroethyl)-1H-pyrrole-2-carboxylate

Product 2

HCID 90406393methyl 1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylateHCID 90406942methyl 1-(4-chlorophenyl)-3-(perfluoroethyl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methyl 3-(trifluoromethyl)-1H-pyrrole-2-carboxylate and methyl 3-(perfluoroethyl)-1H-pyrrole-2-carboxylate (300 mg, 1.55 mmol, 1.00 equiv), (4-chlorophenyl)boronic acid (727 mg, 4.65 mmol, 3.00 equiv), Cu(AcO)2 (562 mg, 2.00 equiv), pyridine (491 mg, 6.21 mmol, 4.00 equiv) and dichloromethane (20 mL). The resulting solution was stirred for 2d at 20° C. The solids were filtered out. The resulting residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:15) to yield methyl 1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate and methyl 1-(4-chlorophenyl)-3-(perfluoroethyl)-1H-pyrrole-2-carboxylate as yellow oil.

Workup

  1. customInto a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. filtrationThe solids were filtered out

Sources & evidence

ORD record
ord-6561257292c643f295fbe52a1105b5f3
Source dataset
uspto-grants-2014_12
Patent number
US08912227B1

Reaction notes

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