Tetrabutylammonium Fluoride → HCID 11965535, compound

HRID 1894046Notes

Reaction equation

HRID 1894046 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[N:12][N:13]([CH2:15][Si](C)(C)C)[CH:14]=2)[C:7]([C:20]([F:23])([F:22])[F:21])=[CH:6][C:5]=1[NH2:24].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[N:12][N:13]([CH3:15])[CH:14]=2)[C:7]([C:20]([F:23])([F:21])[F:22])=[CH:6][C:5]=1[NH2:24]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59164522HCID 59164522, compound

Product 1

HCID 11965535HCID 11965535, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Amino-4-trifluoromethyl-5-(1-trimethylsilanylmethyl-1H-[1,2,3]triazol-4-yl)-benzoic acid methyl ester (420 mg, 1.12 mmol) was dissolved in THF (10 mL). After addition of a solution of TBAF in THF (1M, 2.25 mL, 2 equiv), the mixture was stirred at r.t. for 30 min. The solvent was removed in vacuo and the residue was taken in AcOEt. The organic phase was washed with water, dried (Na2SO4) and concentrated in vacuo to give a brown oil. The crude product was purified by flash chromatography (EtOAc/hexanes (1:9) to EtOAc/hexanes (6:4)) to yield 2-amino-5-(1-methyl-1H-[1,2,3]triazol-4-yl)-4-trifluoromethyl-benzoic acid methyl ester (240 mg, 71%) as a yellow solid. (ESI-MS: m/z 301.3 [M+H]+, rt 4.62 min).

Workup

  1. customThe solvent was removed in vacuo
  2. washThe organic phase was washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give a brown oil
  6. customThe crude product was purified by flash chromatography (EtOAc/hexanes (1:9) to EtOAc/hexanes (6:4))

Sources & evidence

ORD record
ord-689c841d79e54beaae7ed75c09acb74e
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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