Borane → HCID 70978261, compound

HRID 1754106Notes

Reaction equation

HRID 1754106 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1)(=[O:12])=[O:11].B>C1COCC1>[F:22][C:2]([F:1])([F:21])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 6331Borane2×HCID 70978252HCID 70978252, compound

Product 1

HCID 70978261HCID 70978261, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 100 mL round-bottomed flask was added 4-(2-(trifluoromethoxy)phenylsulfonyl)benzonitrile (900 mg, 2.75 mmol) in THF (Volume: 25 mL) to give a colorless solution. Borane (1 molar in THF, 6.87 mL, 6.87 mmol) was added and the mixture heated to reflux and monitored by TLC. TLC appeared to show little reaction after 3 hours, so heated overnight. TLC did not change so added 2 additional equivalents of borane and refluxed for an additional two hours. The reaction was then cooled and slowly quenched with methanol. The reaction was diluted with ethyl acetate and poured into a separatory funnel. The organic layer was washed with 2M NaOH, water, and saturated, aqueous sodium chloride. The organic was separated, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 927.8 mg of crude product. Material purified on Biotage to give 422.0 mg of product (46% yield).

Workup

  1. customto give a colorless solution
  2. temperaturethe mixture heated
  3. temperatureto reflux
  4. customreaction after 3 hours
  5. customso heated overnight
  6. temperaturerefluxed for an additional two hours
  7. temperatureThe reaction was then cooled
  8. customslowly quenched with methanol
  9. additionThe reaction was diluted with ethyl acetate
  10. additionpoured into a separatory funnel
  11. washThe organic layer was washed with 2M NaOH, water
  12. customThe organic was separated
  13. dry with materialdried with anhydrous magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated under reduced pressure
  16. customto give 927.8 mg of crude product
  17. customMaterial purified on Biotage

Sources & evidence

ORD record
ord-ad9150f0f9f84140844657cff6c02c1e
Source dataset
uspto-grants-2015_10
Patent number
US09169209B2

Reaction notes

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