Borane;tetrahydrofuran → HCID 59395056, compound

HRID 2404905Notes

Reaction equation

HRID 2404905 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](O)([C:12]([F:15])([F:14])[F:13])[C:7](=O)[NH:8]2)=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1.CN(C=O)C>[F:15][C:12]([F:13])([F:14])[C:6]1[C:5]2[C:9](=[CH:10][C:2]([NH2:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1

Participants

5

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 59395032HCID 59395032, compound

Product 1

HCID 59395056HCID 59395056, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-amino-3-hydroxy-3-(trifluoromethyl)indolin-2-one (58 mg, 0.25 mmol) in THF (0.5 mL) at 0° C. was added BH3.THF complex (1 M in THF, 1 mL, 0.95 mmol) dropwise. The reaction mixture was stirred for 5 min at 0° C. then for 3 h at room temperature. The reaction mixture was quenched by adding very carefully 6M HCl (3.5 mL) until no more gas release was observed. The reaction mixture was then stirred at 80° C. for 2 h. The solvent was removed under reduce pressure and the solid residue obtained was dissolved in DMF (3 mL), filtered and purified by reverse phase HPLC (10-99% CH3CN/H2O) to provide 3-(trifluoromethyl)-1H-indol-6-amine (30 mg, 54%, TFA salt).

Workup

  1. waitfor 3 h at room temperature
  2. customThe reaction mixture was quenched
  3. additionby adding very carefully 6M HCl (3.5 mL) until no more gas release
  4. stirringThe reaction mixture was then stirred at 80° C. for 2 h
  5. customThe solvent was removed
  6. customthe solid residue obtained
  7. filtrationfiltered
  8. custompurified by reverse phase HPLC (10-99% CH3CN/H2O)

Sources & evidence

ORD record
ord-bb9ec5a74e6f4f3e8b6bf6ede8f621f7
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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