Triethylamine → Ethyl 4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate

HRID 1845189Notes

Reaction equation

HRID 1845189 reaction equation
Cl[C:2]([C:4]1[CH:5]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH:9]=1)=[O:3].[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2[CH:9]=[C:4]([C:2]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:3])[CH:5]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 58187974Ethyl 5-(chlorocarbonyl)-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 58188240Ethyl 4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 5-(chlorocarbonyl)-4′-methylbiphenyl-3-carboxylate (5.5 g, 18 mmol) in methylene chloride (100 mL) at 0° C. were slowly added pyrrolidine (2.6 g, 36 mmol) and triethylamine (7.6 mL, 54 mmol). The mixture was stirred at room temperature for 2 h, and then washed with brine, aq. Na2CO3 solution and water. The separated organic phase was dried (Na2SO4), and concentrated. The residue was purified by silica gel column (30-100% EtOAc/hexane) to afford the desired compound.

Workup

  1. customat 0° C.
  2. washwashed with brine, aq. Na2CO3 solution and water
  3. dry with materialThe separated organic phase was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column (30-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-b2d0a68ac6244d46bcafa90aa6c0a65b
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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