Dimethyl Sulfoxide → Methyl 2-(4-fluorophenyl)-3-(3-(methoxymethyl)piperidin-1-yl)quinoxaline-6-carboxylate

HRID 717031Notes

Reaction equation

HRID 717031 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][NH:7][CH2:6]1.C[O-].[Na+].Cl[C:15]1[C:16]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[N:17][C:18]2[C:23]([N:24]=1)=[CH:22][C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:20][CH:19]=2.CS(C)=O>ClCCl.O>[F:35][C:32]1[CH:31]=[CH:30][C:29]([C:16]2[C:15]([N:7]3[CH2:8][CH2:9][CH2:10][CH:5]([CH2:4][O:3][CH3:2])[CH2:6]3)=[N:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=3)[N:17]=2)=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10942334Sodium MethoxideHCID 171780523-(Methoxymethyl)piperidine hydrochlorideHCID 77231184Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

Product 1

HCID 67042016Methyl 2-(4-fluorophenyl)-3-(3-(methoxymethyl)piperidin-1-yl)quinoxaline-6-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL sealed tube, was placed a solution of 3-(methoxymethyl)piperidine hydrochloride (170 mg, 1.03 mmol, 2.00 equiv) in dichloromethane (7 mL), and sodium methoxide (128 mg, 2.37 mmol, 5.00 equiv). The resulting solution was stirred for 3 h at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum and was added into a 8-mL sealed tube with methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (150 mg, 0.47 mmol, 1.00 equiv) and DMSO (4 mL). The mixture was stirred overnight at 100° C. Water was added to quench the reaction and the resulting solids were collected by filtration. The residue was purified by silica gel column chromatography with PE/EA (50:1). This resulted in 179.9 mg (88%) of methyl 2-(4-fluorophenyl)-3-(3-(methoxymethyl)piperidin-1-yl)quinoxaline-6-carboxylate as a yellow solid.

Workup

  1. customInto a 50-mL sealed tube
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. additionwas added into a 8-mL
  5. stirringThe mixture was stirred overnight at 100° C
  6. customto quench
  7. customthe reaction
  8. filtrationthe resulting solids were collected by filtration
  9. customThe residue was purified by silica gel column chromatography with PE/EA (50:1)
  10. customThis resulted in 179.9 mg (88%) of methyl 2-(4-fluorophenyl)-3-(3-(methoxymethyl)piperidin-1-yl)quinoxaline-6-carboxylate as a yellow solid

Sources & evidence

ORD record
ord-0087a8c85d2c4abebde5f223ea51c542
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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