Boron tribromide → HCID 135520466, compound

HRID 1821648Notes

Reaction equation

HRID 1821648 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([O:26]C)=[C:21]([CH:25]=3)[C:22]([OH:24])=[O:23])[N:15]=2)[NH:10][C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([OH:26])=[C:21]([CH:25]=3)[C:22]([OH:24])=[O:23])[N:15]=2)[NH:10][C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11689341HCID 11689341, compound

Product 1

HCID 135520466HCID 135520466, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-(3-Benzyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)-2-methoxybenzoic acid (105.9 mg, 0.282 mmol) in DCM (10 mL) at −78° C. was added BBr3 (1 M in DCM, 0.563 mL, 0.563 mmol) in a dropwise fashion. The mixture was allowed to warm to room temperature and stirred vigorously for 16 hours. After concentration under reduced pressure, the residue thus obtained was purified by column chromatography [silica gel; MeOH/DCM (1:9)] to give the product as a brown powder (82 mg, 80%). 1H NMR (400 MHz, DMSO): δ 12.02 (s, 1H), 8.34-8.33 (m, 2H), 7.87 (dd, J=3.0, 11.6 Hz, 1H), 7.41-7.27 (m, 5H), 6.77 (d, J=12.0 Hz, 1H), 5.07 (s, 2H). MS: 363.1 (M+H).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue thus obtained
  3. customwas purified by column chromatography [silica gel; MeOH/DCM (1:9)]

Sources & evidence

ORD record
ord-1893fdd7f9a642a8a38c2401fa4166af
Source dataset
uspto-grants-2009_10
Patent number
US07608622B2

Reaction notes

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