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

HRID 1404160Notes

Reaction equation

HRID 1404160 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].[Cl:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.N1C=CC=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([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:17][CH:16]=1

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of the product prepared in Step B (1160 mg, 6.0 mmol, 1 eq), 4-chlorophenylboronic acid (2.9 g, 18.0 mmol, 1 eq), Cu(OAc)2 (2.18 g, 12.0 mmol, 2 eq), 4A molecular sieves (3 g), pyridine (1.94 mL, 4.0 mmol, 4 eq) in DCM (40 mL) was stirred at room temperature for 2 days. The resulting suspension was filtered through CELITE, washed with DCM, and concentrated. The resulting residue was dry packed and purified by flash chromatography (120 g column) eluting with 4 to 8% EtOAc/heptane to yield methyl 1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate.

Workup

  1. filtrationThe resulting suspension was filtered through CELITE
  2. washwashed with DCM
  3. concentrationconcentrated
  4. customThe resulting residue was dry
  5. custompurified by flash chromatography (120 g column)
  6. washeluting with 4 to 8% EtOAc/heptane

Sources & evidence

ORD record
ord-24ce7914fa8e4c1b9a0e0509fd4a80c8
Source dataset
uspto-grants-2014_12
Patent number
US08912227B1

Reaction notes

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