Pyridine → Methyl 3-tert-butyl-5-cyanobenzoate

HRID 1640141Notes

Reaction equation

HRID 1640141 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=O.N1C=CC=CC=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C1COCC1>[C:14]([C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([C:2]#[N:1])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 24728008Methyl 3-tert-butyl-5-carbamoylbenzoate

Product 1

HCID 24729630Methyl 3-tert-butyl-5-cyanobenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of give methyl 3-(aminocarbonyl)-5-tert-butylbenzoate (11.8 g, 0.0451 mol) in THF (88) was added pyridine (5.5 mL, 0.068 mol) and TFAA (9.6 mL, 0.068 mol). The reaction mixture was allowed to stir at rt for 3 h and then quenched by the addition of aq sat NaHCO3 and brine. The mixture was extracted with EtOAc. The organic solutions were combined and washed with sodium bicarbonate, brine, 1M HCl, water and brine. The solution was dried over MgSO4, filtered, and concentrated to give methyl 3tert-butyl-5-cyanobenzoate (9.5 g, 70% pure, 68%). 1H NMR (400 MHz, d6-DMSO) δ: 8.77 (s, 1H), 8.48 (s, 1H), 8.19 (m, 1H), 8.17 (m, 1H), 8.15 (1, m), 3.88 (s, 3H), and 1.31 (s, 9H). LCMS: ES+ 218.2

Workup

  1. customquenched by the addition
  2. extractionThe mixture was extracted with EtOAc
  3. washwashed with sodium bicarbonate, brine, 1M HCl, water and brine
  4. dry with materialThe solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a364e8f0ecaf4fb5af343a7460b9093f
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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