Phosphorus tribromide → HCID 90386835, compound

HRID 1476806Notes

Reaction equation

HRID 1476806 reaction equation
O[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([C:13]#[N:14])[N:4]=1.P(Br)(Br)[Br:16].C([O-])(O)=O.[Na+]>C1COCC1>[Br:16][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([C:13]#[N:14])[N:4]=1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 90386955HCID 90386955, compound

Product 1

HCID 90386835HCID 90386835, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1-(hydroxymethyl)isoquinoline-3-carbonitrile (0.150 g, 0.814 mmol) in THF (0.8 mL) and treated with PBr3 (0.814 mL, 0.814 mmol). The reaction mixture was stirred at RT for 2 hours, then poured over ice and neutralized with saturated aqueous NaHCO3. The mixture was warmed to RT and extracted with EtOAc (20 mL). The organic phase was separated, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as a yellow solid. The crude product was dried under high vacuum and used without further purification (0.15 g, 75%). ESI-MS m/z [M+H]+ 247.5.

Workup

  1. temperatureThe mixture was warmed to RT
  2. extractionextracted with EtOAc (20 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f23df9fae6042dab3ba08aa397a0361
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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