Phosphorus tribromide → HCID 86685994, compound

HRID 2277700Notes

Reaction equation

HRID 2277700 reaction equation
P(Br)(Br)[Br:2].[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH:23](O)[CH3:24])[CH:22]=1)[CH2:10][CH2:9]2>C(Cl)Cl>[Br:2][CH:23]([C:21]1[CH:22]=[C:17]([N:11]2[CH2:10][CH2:9][C:8]3[C:13](=[CH:14][CH:15]=[C:6]([Cl:5])[CH:7]=3)[C:12]2=[O:16])[CH:18]=[N:19][CH:20]=1)[CH3:24]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 86685995HCID 86685995, compound

Product 1

HCID 86685994HCID 86685994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PBr3 (541 mg, 2 mmol) was added dropwise into a solution of 6-chloro-2-[5-(1-hydroxy-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-isoquinolin-1-one (example 13) (302 mg, 1 mmol) in 5 mL DCM at 0° C. The reaction was stirred at RT for 2 hours before it was neutralized with satd. aq. NaHCO3 solution and extracted with DCM (10 mL, 2×). The organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to afford a crude product as an oil which was used in the next step without further purification (380 mg, 100%). MS: 365.2 (M+H)+.

Workup

  1. extractionaq. NaHCO3 solution and extracted with DCM (10 mL, 2×)
  2. washThe organic layers were washed with brine
  3. customdried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f664c6a033d34127a830f522ca723742
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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