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Dichloromethane → Methyl 3-(5-methylpyridin-2-yl)-5-(1-methyl-1H-1,2,3-triazol-5-yl)benzoate

HRID 888387
Notes
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Reaction equation

HRID 888387 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([C:18]3[N:22]([CH2:23][Si](C)(C)C)[N:21]=[N:20][CH:19]=3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.[Cl-].[NH4+]>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([C:18]3[N:22]([CH3:23])[N:21]=[N:20][CH:19]=3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 68496792Methyl 3-(5-methylpyridin-2-yl)-5-(1-((trimethylsilyl)methyl)-1H-1,2,3-triazol-5-yl)benzoate

Product 1

HCID 68500364Methyl 3-(5-methylpyridin-2-yl)-5-(1-methyl-1H-1,2,3-triazol-5-yl)benzoateYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 3-(5-methylpyridin-2-yl)-5-{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-5-yl}benzoate (122 mg, 0.321 mmol) in THF (5 mL) was added 2 M tetrabutylammonium fluoride in THF (1.60 mL, 3.20 mmol). After 16 h, the mixture was distributed between 100 ml of dichloromethane and 100 ml of 1 M ammonium chloride solution. The organic layer was washed with 50 mL of brine and concentrated to give title compound (85 mg). MS 309.1 (M+1).

Workup

  1. washThe organic layer was washed with 50 mL of brine
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-016d9e0aaec04c69b4485ac15310600f
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08247401B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes