Diisopropylamine → Ethyl 1-(4-fluorophenyl)-2-((2-(trifluoromethyl)phenyl)ethynyl)-1H-imidazole-5-carboxylate

HRID 2368506Notes

Reaction equation

HRID 2368506 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[C:9]#[C:10][C:11]1[N:12]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:15]=1.FC1C=CC(N2C(C(OCC)=O)=CN=C2I)=CC=1.C(C1C=CC=CC=1[C:54]([F:57])([F:56])[F:55])#C.C(NC(C)C)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C1COCC1>[F:27][C:24]1[CH:23]=[CH:22][C:21]([N:12]2[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:15]=[C:11]2[C:10]#[C:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:54]([F:57])([F:56])[F:55])=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 41008561-Ethynyl-2-(trifluoromethyl)benzeneHCID 71117744ethyl 1-(4-fluorophenyl)-2-iodo-1H-imidazole-5-carboxylateHCID 71119630ethyl 2-((2-chloro-6-fluorophenyl)ethynyl)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate

Product 1

HCID 71117657Ethyl 1-(4-fluorophenyl)-2-((2-(trifluoromethyl)phenyl)ethynyl)-1H-imidazole-5-carboxylate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-(4-fluorophenyl)-2-((2-(trifluoromethyl)phenyl)ethynyl)-1H-imidazole-5-carboxylate (46) was prepared in a similar manner as that described for the synthesis of compound 42 using ethyl 1-(4-fluorophenyl)-2-iodo-1H-imidazole-5-carboxylate (38) (900 mg, 2.5 mmol), 1-ethynyl-2-(trifluoromethyl)benzene (0.42 mL, 3.0 mmol), PdCl2(PPh3)2 (88 mg, 0.13 mmol), copper (I) iodide (23 mg, 0.13 mmol), diisopropyl amine (7 mL), and THF (50 mL).

Sources & evidence

ORD record
ord-93a1d828a72848ffb78bbdd6e2b7b112
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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