Hydrochloric Acid → HCID 59536404, compound

HRID 445316Notes

Reaction equation

HRID 445316 reaction equation
O1CCCC1.B.[CH2:7]([N:14]1[C:23](=O)[C:22]([F:26])([F:25])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]1[C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C1COCC1>[CH2:7]([N:14]1[CH2:23][C:22]([F:26])([F:25])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]1[C:27]1[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 59536369HCID 59536369, compound

Product 1

HCID 59536404HCID 59536404, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of borane tetrahydrofuran complex (1M in THF, 0.750 mL, 0.750 mmol) in 5 mL of THF, 2-benzyl-4,4-difluoro-1-(4-(trifluoromethyl)-phenyl)-1,2-dihydroisoquinolin-3(4H)-one (0.103 g, 0.246 mmol) in a total of 5 mL THF was added dropwise. The clear solution was refluxed for 5 h. After the reaction mixture was cooled to 0° C., 5 mL of 5 N hydrochloric acid was added. The solution was stirred at 0° C. to RT over 1 h. Then the most organic solvent was evaporated and the pH was adjusted to ˜8 by solid sodium bicarbonate. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with water and saturated aqueous sodium chloride. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a white solid. 11-1 NMR (300 MHz, CHLOROFORM-d) δ ppm 7.76 (d, J=7.75 Hz, 1H) 7.62 (d, J=8.18 Hz, 2H) 7.46 (d, J=8.04 Hz, 2H) 7.28-7.42 (m, 7H) 6.77 (d, J=7.75 Hz, 1H) 4.80 (d, J=3.65 Hz, 1H) 3.82 (dd, J=13.59, 1.75 Hz, 1H) 3.37-3.54 (m, 2H) 2.87-3.06 (m, 1H).

Workup

  1. temperatureThe clear solution was refluxed for 5 h
  2. customThen the most organic solvent was evaporated
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washThe combined organic phases were washed with water and saturated aqueous sodium chloride
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34da07dfbfa948f8a3f9119e1c6f8375
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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