Phosphorus tribromide → 3-(1-Bromoethyl)-4-(5-(morpholinomethyl)thiophen-2-yl)-1H-isochromen-1-one hydrobromide

HRID 634397Notes

Reaction equation

HRID 634397 reaction equation
P(Br)(Br)[Br:2].O[CH:6]([C:8]1[O:9][C:10](=[O:30])[C:11]2[C:16]([C:17]=1[C:18]1[S:19][C:20]([CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:21][CH:22]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:7]>C(Cl)Cl>[BrH:2].[Br:2][CH:6]([C:8]1[O:9][C:10](=[O:30])[C:11]2[C:16]([C:17]=1[C:18]1[S:19][C:20]([CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:21][CH:22]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:7]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 1181311513-(1-Hydroxyethyl)-4-(5-(morpholinomethyl)thiophen-2-yl)-1H-isochromen-1-one2×

Product 1

HCID 1181312913-(1-Bromoethyl)-4-(5-(morpholinomethyl)thiophen-2-yl)-1H-isochromen-1-one hydrobromideYield 38.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1M PBr3 in DCM (1.82 mL, 1.82 mmol) was added to 3-(1-hydroxyethyl)-4-(5-(morpholinomethyl)thiophen-2-yl)-1H-isochromen-1-one (intermediate B16, 258 mg, 0.695 mmol) in DCM (2.6 ml) at RT. The reaction mixture concentrated under reduced pressure and the crude was crystallized from boiling DCM/MeOH 4/1 (5 ml) to give the title compound as colourless solid (138 mg, 38.6%)

Workup

  1. concentrationThe reaction mixture concentrated under reduced pressure
  2. customthe crude was crystallized

Sources & evidence

ORD record
ord-bc8f5a2b5edc4778a75cfee55cf14a6d
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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