Phosphorus tribromide → HCID 118131409, compound

HRID 634395Notes

Reaction equation

HRID 634395 reaction equation
P(Br)(Br)[Br:2].O[CH:6]([C:8]1[O:9][C:10](=[O:25])[C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([CH3:24])[CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:7]>C(Cl)Cl>[Br:2][CH:6]([C:8]1[O:9][C:10](=[O:25])[C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([CH3:24])[CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:7]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 118131074HCID 118131074, compound

Product 1

HCID 118131409HCID 118131409, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1 M PBr3 in DCM (846 μL, 0.846 mmol) was added to of 3-(1-hydroxyethyl)-4-(2-methylpyridin-4-yl)-1H-isochromen-1-one (intermediate B13, 140 mg, 0.498 mmol) in DCM at RT. Reaction mixture was concentrated under reduced pressure and straightforward purified via reverse phase chromatography with a Biotage C18 SNAP 60 g column (Phase A, water 95%, ACN 4.5%, formic acid 0.5%); Phase B ACN 99.5%, formic acid 0.5%) to give the title compound (80 mg, 45%).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customstraightforward purified via reverse phase chromatography with a Biotage C18 SNAP 60 g column (Phase A, water 95%, ACN 4.5%, formic acid 0.5%)

Sources & evidence

ORD record
ord-acc40668035740cb827321e5dc993c5d
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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