Acetonitrile → Ethyl 4-(6-methoxyquinolin-2-yl)cyclohexanecarboxylate

HRID 55784

Reaction equation

HRID 55784 reaction equation
N1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.Cl[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=2)[N:14]=1.[CH3:25]C#N>>[CH3:24][O:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH:25]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1)[CH:22]=[CH:21]2

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 70770Ethyl 4-piperidinecarboxylateHCID 836472-Chloro-6-methoxyquinoline2×

Product 1

HCID 66980031Ethyl 4-(6-methoxyquinolin-2-yl)cyclohexanecarboxylate

Procedure

Ethyl piperidine-4-carboxylate (100 mg) was treated with 2-chloro-6-methoxyquinoline (Intermediate 1) (90 mg) in MeCN (0.8 mL) and TEA (100 mg) in a sealed tube at 180° C. for 6 h in a microwave reactor. After aqueous work-up with EtOAc and column purification, eluting with EtOAc/hexane, ethyl 4-(6-methoxyquinolin-2-yl)cyclohexanecarboxylate (90 mg) was afforded as a solid.

Workup

  1. customAfter aqueous work-up with EtOAc and column purification
  2. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-550c1e91025842e7bcb55db1293d04a9
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Linked notes

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