Boron tribromide → HCID 24988364, compound

HRID 643014Notes

Reaction equation

HRID 643014 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28]C)[C:23]4=[O:30])=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[C:23]4=[O:30])=[CH:20][CH:21]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57640508HCID 57640508, compound

Product 1

HCID 24988364HCID 24988364, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Chloro-N-((1-(4-(3-methoxy-2-oxopyridin-1(2H)-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide (306 mg, 0.69 mmol, prepared using a similar procedure as described in Example 4) was stirred in 40 mL DCM as a slurry. BBr3 (200 μL, 2.1 mmol) was added. The mixture was stirred for 2 hrs and concentrated in vacuo. The residue was dissolved in 1 mL and 5 mL DMSO and subjected to prep HPLC to isolate the title compound as a white powder. MS found for C19H14ClN5O3S (M+H)+ 428.1, 430.1 (Cl pattern).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in 1 mL and 5 mL DMSO

Sources & evidence

ORD record
ord-06a96cf62b654737b41d01dea72ffdae
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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