HCID 71257872, compound → HCID 71257878, compound

HRID 337312Notes

Reaction equation

HRID 337312 reaction equation
C([NH:5][C:6](=[O:19])[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:9][C:8]=1[F:18])(C)(C)C>C(O)(C(F)(F)F)=O>[C:14]([C:10]1[CH:11]=[C:12]([CH3:13])[C:7]([C:6]([NH2:5])=[O:19])=[C:8]([F:18])[CH:9]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 1

HCID 71257872HCID 71257872, compound

Product 1

HCID 71257878HCID 71257878, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N,4-di-tert-butyl-2-fluoro-6-methylbenzamide (4.01 g, 15.1 mmol, Eq: 1.00) in TFA (48 ml) (4×12 mL, microwave vials) was stirred at 100° C. for 3 h under microwave assisted conditions. The contents of the four microwave vials were combined, evaporated under vacuum and residue was poured (carefully) into an aqueous saturated solution of NaHCO3 (100 mL) and the product was extracted with CH2Cl2 (2×100 mL). The combined organic extracts were dried (Na2SO4) and evaporated under vacuum. The crude material was purified by chromatography (SiO2, CH2Cl2 100% to 30% AcOEt, in 30 min) to afford the desired product (2.55 g, 81% yield as a white solid. LC/MS, m/z 210[M+H]+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.32 (s, 9 H) 2.49 (t, J=0.63 Hz, 3 H) 5.86 (br. s., 2 H) 6.94-7.00 (m, 1 H) 7.05 (dd, J=1.26, 0.51 Hz, 1 H).

Workup

  1. customevaporated under vacuum and residue
  2. additionwas poured (carefully) into an aqueous saturated solution of NaHCO3 (100 mL)
  3. extractionthe product was extracted with CH2Cl2 (2×100 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. customevaporated under vacuum
  6. customThe crude material was purified by chromatography (SiO2, CH2Cl2 100% to 30% AcOEt, in 30 min)

Sources & evidence

ORD record
ord-e36daac1efb341b6a06cf4a529b53e30
Source dataset
uspto-grants-2014_11
Patent number
US08889682B2

Reaction notes

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