Boron tribromide → HCID 136006496, compound

HRID 384359Notes

Reaction equation

HRID 384359 reaction equation
C[O:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:17][CH2:18][CH2:19][N:20]=2)=[CH:12][CH:11]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[CH:12][C:13]([N:20]2[CH2:19][CH2:18][N:17]=[CH:16]2)=[CH:14][CH:15]=1.[OH:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[CH:12][C:13]([C:16]2[NH:20][CH2:19][CH2:18][N:17]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 59615671HCID 59615671, compound

Product 2

HCID 86648900HCID 86648900, compoundHCID 136006496HCID 136006496, compoundYield 173.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(2′-Methoxy-3′-amino-biphenyl-4-yl)-4,5-dihydro-1H-imidazol 32c (1.1 g, 4.1 mmol) was dissolved in 50 mL of dichloromethane at room temperature, followed by addition of a solution of boron tribromide in dichloromethane (1 N, 16.5 mL). The reaction mixture was stirred at room temperature for 4 hours. The reaction was monitored by TLC until the disappearance of the starting materials and then quenched with methanol. The mixture was concentrated under reduced pressure. The residue was dissolved in 10 mL of ethyl acetate and stirred for 30 minutes. The mixture was filtered and the filter cake was washed with ethyl acetate (5 mL×2) and dried to obtained the title compound 2-(2′-hydroxy-3′-amino-biphenyl-4-yl)-4,5-dihydro-1H-imidazol 32d (900 mg, 89.6%) as a grey solid.

Workup

  1. customquenched with methanol
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 10 mL of ethyl acetate
  4. stirringstirred for 30 minutes
  5. filtrationThe mixture was filtered
  6. washthe filter cake was washed with ethyl acetate (5 mL×2)
  7. customdried

Sources & evidence

ORD record
ord-11656add054a4d6cb5400bffd64d10bf
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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