Ethyl Acetate → HCID 178432894, compound

HRID 2359990Notes

Reaction equation

HRID 2359990 reaction equation
[NH:1]1[C:5]([CH2:6][C:7]2[N:8]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[C:9]([C:12]3[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=3)=[CH:10][CH:11]=2)=[N:4][N:3]=[N:2]1.[CH3:26][C:27]1[NH:28][CH:29]=[CH:30][N:31]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC(=O)OCC>CS(C)=O>[NH:1]1[C:5]([CH2:6][C:7]2[N:8]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[C:9]([C:12]3[CH:17]=[CH:16][C:15]([N:28]4[CH:29]=[CH:30][N:31]=[C:27]4[CH3:26])=[CH:14][CH:13]=3)=[CH:10][CH:11]=2)=[N:4][N:3]=[N:2]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 127492-MethylimidazoleHCID 178516227HCID 178516227, compound

Product 1

HCID 178432894HCID 178432894, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 4-(2-((1H-tetrazol-5-yl)methyl)-5-(4-bromophenyl)-1H-pyrrol-1-yl)phenol (1.0 g, 2.52 mmol) and 2-methyl-1H-imidazole (2.07 g, 25.2 mmol) in DMSO (10.0 mL) was added 8-HQ (54 mg, 0.38 mmol), Cu2O (0.29 g, 2.52 mmol), Cs2CO3 (0.986 g, 3.03 mmol) and PEG-2000 (0.29 g). The resultant mixture was heated at 150° C. for 3 h under microwave irradiation. The mixture was treated with EA (60 mL), the resultant precipitate was filtered and purified by Biotage-flash (Solid phase: C18; Mobile phase: A: CH3CN, B: H2O (0.05% CF3COOH); gradient: 12%→24% B in A; flow rate: 40 mL/min) to afford an off white solid (143 mg, yield 14%)

Workup

  1. filtrationthe resultant precipitate was filtered
  2. custompurified by Biotage-flash (Solid phase

Sources & evidence

ORD record
ord-90bf7582842d46d599808ab71d48cd6a
Source dataset
uspto-grants-2014_04
Patent number
US08686015B2

Reaction notes

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