Boron trifluoride → HCID 178474393, compound

HRID 873030Notes

Reaction equation

HRID 873030 reaction equation
[CH2:1]([C:8]1[C:9]([NH:24][C:25](=[O:27])[CH3:26])=[N:10][C:11]2[CH:12]=[CH:13][C:14]3[CH:21]=[C:20]([O:22]C)[CH:19]=[CH:18][C:15]=3[C:16]=2[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(F)(F)F.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([C:8]1[C:9]([NH:24][C:25](=[O:27])[CH3:26])=[N:10][C:11]2[CH:12]=[CH:13][C:14]3[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:15]=3[C:16]=2[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 516892Sodium BicarbonateHCID 70662806N-(2-benzyl-8-methoxybenzo[f]quinoxalin-3-yl)acetamide

Product 1

HCID 178474393HCID 178474393, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, to a suspension of N-(2-benzyl-8-methoxybenzo[f]quinoxalin-3-yl)acetamide (60.0 mg, 168 μmol) in anhydrous dichloromethane (2 mL) was added boron trifluoride (1.0 M in dichloromethane) (840 μL, 840 μmol) at 0° C. After elevating to room temperature, the mixture was stirred for 3 hours. To the mixture was then added a solution of saturated sodium hydrogencarbonate, and the product was extracted with ethyl acetate (×3). The combined organic extract was washed successively with water (×1) and brine (×1), followed by drying over anhydrous sodium sulfate. Filtration and concentration under reduced pressure gave N-(2-benzyl-8-hydroxybenzo[f]quinoxalin-3-yl)acetamide (13) as a crude yellow solid product. The product was used for the subsequent reaction without any further purification. TLC Rf=0.36 (n-hexane/ethyl acetate=1/2); 1H NMR (500 MHz, CD3OD) δ 2.17 (s, 3H), 4.50 (s, 2H), 7.20-7.32 (m, 9H), 7.78 (d, 1H, J=9.0 Hz), 7.96 (d, 1H, J=9.0 Hz), 9.44 (d, 1H, J=7.5 Hz).

Workup

  1. customAfter elevating to room temperature
  2. extractionthe product was extracted with ethyl acetate (×3)
  3. extractionThe combined organic extract
  4. washwas washed successively with water (×1) and brine (×1)
  5. dry with materialby drying over anhydrous sodium sulfate
  6. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-f713bd9ea1f446708407bddda69cf511
Source dataset
uspto-grants-2015_03
Patent number
US08975403B2

Reaction notes

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