Tetrafluoroboric acid → HCID 11152242, compound

HRID 736397Notes

Reaction equation

HRID 736397 reaction equation
N[C:2]1[C:3]([C:8]2[CH:26]=[CH:25][C:11]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=3)=[O:13])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.N([O-])=O.[Na+].[H+].[B-](F)(F)(F)[F:33]>O>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12](=[O:13])[C:11]2[CH:25]=[CH:26][C:8]([C:3]3[C:2]([F:33])=[CH:7][CH:6]=[CH:5][N:4]=3)=[CH:9][CH:10]=2)=[CH:16][CH:17]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 10382943HCID 10382943, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 11152242HCID 11152242, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The product from Example 3 (52.0 mg, 0.145 mmol) in 48% HBF4 (0.75 mL) and water (0.1 mL) was treated with solid NaNO2 (11.9 mg, 0.172 mmol) at 0° C. After stirring for 30 minutes, the layers were allowed to separate and the liquid was layer was removed by pipette. The remaining solid was dried under reduced pressure and slurried in toluene (1.5 mL). The suspension was heated at 100° C. for 2.5 hours, allowed to cool to room temperature, and the toluene was removed by pipette. The residue was treated with 1N NaOH (1 mL) and CHCl3 (1 mL) and stirred for 15 minutes. The phases were allowed to separate and the aqueous layer was extracted with CHCl3 (2×1 mL). The organic layers were combined, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (20% ethyl acetate in hexanes) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 8.56 (dt, 1H), 8.12 (d, 2H), 7.98 (d, 2H), 7.84 (br s, 1H), 7.59 (d, 2H), 7.53 (ddd, 1H), 7.40 (d, 2H), 7.33 (ddd, 1H), 1.33 (s, 9H); MS (m/z) 349.

Workup

  1. customto separate
  2. customwas removed by pipette
  3. customThe remaining solid was dried under reduced pressure
  4. temperatureto cool to room temperature
  5. customthe toluene was removed by pipette
  6. additionThe residue was treated with 1N NaOH (1 mL) and CHCl3 (1 mL)
  7. stirringstirred for 15 minutes
  8. customto separate
  9. extractionthe aqueous layer was extracted with CHCl3 (2×1 mL)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated under reduced pressure
  13. customThe residue was purified by flash chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5ba6bee2c27a41718323b821635205f1
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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