Phosphorus tribromide → 3-(1-Bromoethyl)-4-(6-methylpyridin-3-yl)-1H-isochromen-1-one hydrobromide

HRID 634391Notes

Reaction equation

HRID 634391 reaction equation
O[CH:2]([C:4]1[O:5][C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[CH:15]=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3].P(Br)(Br)[Br:23]>C(Cl)Cl.CN(C=O)C>[BrH:23].[Br:23][CH:2]([C:4]1[O:5][C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[CH:15]=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 1181311083-(1-Hydroxyethyl)-4-(6-methylpyridin-3-yl)-1H-isochromen-1-one

Product 1

HCID 1181314403-(1-Bromoethyl)-4-(6-methylpyridin-3-yl)-1H-isochromen-1-one hydrobromide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was made in a similar way as that of the intermediate C6, using 3-(1-hydroxyethyl)-4-(6-methylpyridin-3-yl)-1H-isochromen-1-one intermediate B10 (163 mg, 0.579 mmol), 1M PBr3 (0.87 mL, 0.87 mmol) in a mixture of DCM (2 ml) and DMF (3 ml) at RT. The crude was purified via reverse phase chromatography with a Biotage C18 SNAP 60 g column (Phase A, water 95%, ACN 4.9%, formic acid 0.1%); Phase B ACN 99.9%, formic acid 0.1%). The aqueous fractions were added of 50% HBraqueous and concentrated under reduced pressure to give the title compound (320 mg).

Workup

  1. customThe crude was purified via reverse phase chromatography with a Biotage C18 SNAP 60 g column (Phase A, water 95%, ACN 4.9%, formic acid 0.1%)
  2. additionThe aqueous fractions were added of 50% HBraqueous
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f7edd18a5c354cb4a8e24fdefd874901
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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