Boron tribromide → HCID 15951419, compound

HRID 271116Notes

Reaction equation

HRID 271116 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=2)([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15951415HCID 15951415, compound

Product 1

HCID 15951419HCID 15951419, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-amino-5-(3-methoxyphenyl)-3-methyl-5-pyridin-4-yl-3,5-dihydro-4H-imidazol-4-one (0.75 g, 2.5 mmol) in CH2Cl2 (7.5 mL) is added BBr3 (1.0 M in CH2Cl2, 15 mL, 15 mmol) at −78° C. After addition, the reaction mixture is warmed to room temperature and stirred for 3 h. The reaction mixture is poured into ice-water (50 mL) and the two layers are separated. The aqueous is neutralized with 50% aqueous NaOH to pH˜7 and extracted with 4/1 CH2Cl2/2-PrOH (3×100 mL). The combined organic extracts are washed with brine (150 mL), dried (Na2SO4) and concentrated. The resultant residue is purified by chromatography (silica gel, EtOAc/2M methanolic NH3: 95/5) to give the title compound (0.58 g, 79%) as a solid. Mp: 245-247° C.; MS(+) ES: 283 (M+H)+.

Workup

  1. additionAfter addition
  2. customthe two layers are separated
  3. extractionextracted with 4/1 CH2Cl2/2-PrOH (3×100 mL)
  4. washThe combined organic extracts are washed with brine (150 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe resultant residue is purified by chromatography (silica gel, EtOAc/2M methanolic NH3: 95/5)

Sources & evidence

ORD record
ord-147baea6da524b9484832021407666c7
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Reaction notes

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