Borane;tetrahydrofuran → HCID 68283335, compound

HRID 1527486Notes

Reaction equation

HRID 1527486 reaction equation
[Cl:1][C:2]1[C:3]([F:16])=[C:4]([CH:7]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:9]=1)[C:5]#[N:6].B.C1COCC1>C1COCC1>[Cl:1][C:2]1[C:3]([F:16])=[C:4]([CH:7]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:9]=1)[CH2:5][NH2:6]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 68283965HCID 68283965, compound

Product 1

HCID 68283335HCID 68283335, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-Chloro-2-fluoro-5-morpholin-4-yl-benzonitrile (215 mg, 0.85 mmol) in THF (2 mL) was added dropwise a solution of BH3-THF. The reaction mixture was heated under reflux for several hours, cooled to ambient temperature and quenched carefully by addition of methanol. The solvent was removed in vacuo and the crude product was purified by RP-preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 40 mL/min) to give the title compound. MS (LC/MS): 244.9 [M]+; tR (HPLC conditions c): 3.02 min.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for several hours
  3. customquenched carefully by addition of methanol
  4. customThe solvent was removed in vacuo
  5. customthe crude product was purified by RP-preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 40 mL/min)

Sources & evidence

ORD record
ord-234c5e993efd47649d359dda3870c8cc
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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