Borane;tetrahydrofuran → HCID 59395056, compound

HRID 404602Notes

Reaction equation

HRID 404602 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 anhydrous THF (0.5 mL) at 0° C. was added BH3.THF complex (1M in THF) (1 mL, 0.95 mmol, 4 eq) dropwise. The mixture was stirred for 5 min at 0° C. then for 3 h at room temperature. The reaction was quenched by adding very carefully 6M HCl (3.5 mL) until no more gas release was observed. The 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% ACN in water) to give 3-(trifluoromethyl)-1H-indol-6-amine (30 mg, 54%, TFA salt).

Workup

  1. waitfor 3 h at room temperature
  2. customThe reaction was quenched
  3. additionby adding very carefully 6M HCl (3.5 mL) until no more gas release
  4. stirringThe 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% ACN in water)

Sources & evidence

ORD record
ord-ec28e65299334f01b92a69417d3b1078
Source dataset
uspto-grants-2014_06
Patent number
US08748612B2

Reaction notes

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