Boron tribromide → HCID 24830774, compound

HRID 2245926Notes

Reaction equation

HRID 2245926 reaction equation
COC1C=CC(C2(C3N4N=C(C5C=CC=CC=5)C=NC4=NN=3)CC2)=CC=1.C[O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2([C:38]3[N:42]4[N:43]=[CH:44][C:45]([C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=5)=[N:46][C:41]4=[N:40][N:39]=3)[CH2:37][CH2:36]2)=[CH:31][CH:30]=1.B(Br)(Br)Br>C(Cl)Cl>[C:47]1([C:45]2[CH:44]=[N:43][N:42]3[C:38]([C:35]4([C:32]5[CH:31]=[CH:30][C:29]([OH:28])=[CH:34][CH:33]=5)[CH2:37][CH2:36]4)=[N:39][N:40]=[C:41]3[N:46]=2)[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 24178391HCID 24178391, compoundHCID 24830621HCID 24830621, compound

Product 1

HCID 24830774HCID 24830774, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-[1-(4-methoxyphenyl)cyclopropyl]-6-phenyl[1,2,4]triazolo[4,3-b][1,2,4]triazine (17.0 mg, 0.0495 mmol) and 3-[1-(4-methoxyphenyl)cyclopropyl]-7-phenyl[1,2,4]triazolo[4,3-b][1,2,4]triazine (17.0 mg, 0.0495 mmol) in DCM (3.0 mL) was added 1.00 M of boron tribromide in DCM (0.5 mL). The mixture was stirred at RT for 3 h. The solvent was evaporated. The residue was diluted with methanol (5 mL). The resulting mixture was subject to preparative RP-HPLC to give the two regioisomers. Analytical LCMS: (M+H)+=330.1. Isomer-I: Rt=1.451 min; Isomer-II: Rt=1.450 min.

Workup

  1. customThe solvent was evaporated
  2. additionThe residue was diluted with methanol (5 mL)
  3. customto give the two regioisomers

Sources & evidence

ORD record
ord-8cfe3ef2e5194b3981446cc9ae7178ba
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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