Ethyl Acetate → HCID 178426692, compound

HRID 1261413Notes

Reaction equation

HRID 1261413 reaction equation
[NH:1]1C(CC2N(C3C=CC(O)=CC=3)C(C3C=CC(N4C=CN=C4C)=CC=3)=CC=2)=NN=N1.[NH:31]1[C:35]([CH2:36][C:37]2[N:38]([C:49]3C=[CH:53][C:52](O)=[CH:51][CH:50]=3)[C:39]([C:42]3[CH:47]=[CH:46][C:45]([Br:48])=[CH:44][CH:43]=3)=[CH:40][CH:41]=2)=[N:34][N:33]=[N:32]1.CC1NC=CN=1.[C:62]([O-:65])([O-])=O.[Cs+].[Cs+].CC(=O)O[CH2:71][CH3:72]>CS(C)=O>[NH:31]1[C:35]([CH2:36][C:37]2[N:38]([C:49]3[CH:50]=[CH:51][C:52]([C:62]([NH2:1])=[O:65])=[CH:53][C:71]=3[CH3:72])[C:39]([C:42]3[CH:47]=[CH:46][C:45]([Br:48])=[CH:44][CH:43]=3)=[CH:40][CH:41]=2)=[N:34][N:33]=[N:32]1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 127492-MethylimidazoleHCID 178432894HCID 178432894, compoundHCID 178516227HCID 178516227, compound

Product 1

HCID 178426692HCID 178426692, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Representative procedure for Scheme 7: Synthesis of 4-(2-((1H-tetrazol-5-yl)methyl)-5-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-1H-pyrrol-1-yl)phenol. 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-c646e6193865446b8963cbc1627ac66b
Source dataset
uspto-grants-2013_06
Patent number
US08470857B2

Reaction notes

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