Trimethylphosphine → 1-[5-Chloro-8-(3-fluorophenyl)isoquinolin-7-yl]ethanamine

HRID 1192594Notes

Reaction equation

HRID 1192594 reaction equation
[N:1]([CH:4]([C:6]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:14]2[C:9]([CH:10]=[CH:11][N:12]=[CH:13]2)=[C:8]([Cl:23])[CH:7]=1)[CH3:5])=[N+]=[N-].CP(C)C>O1CCCC1.O>[Cl:23][C:8]1[CH:7]=[C:6]([CH:4]([NH2:1])[CH3:5])[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:14]2[C:9]=1[CH:10]=[CH:11][N:12]=[CH:13]2

Participants

5

Reactant 2

HCID 68983TrimethylphosphineHCID 583684257-(1-Azidoethyl)-5-chloro-8-(3-fluorophenyl)isoquinoline

Product 1

HCID 583684511-[5-Chloro-8-(3-fluorophenyl)isoquinolin-7-yl]ethanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 7-(1-azidoethyl)-5-chloro-8-(3-fluorophenyl)isoquinoline (0.105 g, 0.321 mmol) in tetrahydrofuran (2 mL) and water (0.4 mL) was added 1.0 M trimethylphosphine in THF (0.39 mL, 0.39 mmol). The mixture was stirred at room temperature for 1 hour. After nitrogen was passed through the reaction solution, the reaction mixture was extracted with dichloromethane. The extracts were washed with brine, dried over magnesium sulfate and evaporated to dryness. The crude residue was used directly in the next step (75 mg, 78%). LCMS calculated for C17H15ClFN2 (M+H)+: m/z=301.1; Found: 301.1.

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. washThe extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-3092b3a37e83491eac2de9b87f560ad1
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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