Water → HCID 67324388, compound

HRID 1397460Notes

Reaction equation

HRID 1397460 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]([C:19]([CH3:23])([CH3:22])[C:20]#[N:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.O1CCCC1.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][C:10]([C:19]([CH3:23])([CH3:22])[CH2:20][NH2:21])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 2723981Borane;tetrahydrofuranHCID 67323702HCID 67323702, compound

Product 1

HCID 67324388HCID 67324388, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

2-(1-Benzyl-5-phenyl-1H-pyrazol-3-yl)-2-methylpropanenitrile (50 mg, 0.16 mmol) was dissolved in THF (1.6 mL). Borane-tetrahydrofuran (0.8 mL, 1 M solution) was added and the reaction was heated to 60° C. for 3 h. Minimal water was added to quench the reaction. Ethyl acetate was added followed by sodium sulfate and the solids were removed by filtration. The filtrate was concentrated under reduced pressure to yield 2-(1-benzyl-5-phenyl-1H-pyrazol-3-yl)-2-methylpropan-1-amine (50 mg, crude), which was carried through without further purification. MS (ESI) m/z: Calculated for C20H23N3: 305.19. found: 306.2 (M+H)+.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe solids were removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-485cdb2636084b499120fc2458c53055
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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