Cesium carbonate → HCID 86303661, compound

HRID 1476690Notes

Reaction equation

HRID 1476690 reaction equation
ClC1C=CC(B(O)O)=CC=1.BrC1N=CNC=1.Br[C:18]1[N:19]=[CH:20][N:21]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:22]=1.[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([N:21]2[CH:22]=[C:18]([C:31]3[S:30][CH:34]=[CH:33][CH:32]=3)[N:19]=[CH:20]2)=[CH:24][CH:25]=1

Participants

9

Reactant 6

HCID 10796Cesium carbonateHCID 742994-Chlorophenylboronic acidHCID 27339602-Thiopheneboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 66520703HCID 66520703, compound2×HCID 178418934HCID 178418934, compound

Product 1

HCID 86303661HCID 86303661, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

The procedure described above for Formula Ic-iii in Example 16 was followed, starting from 4-chloro-phenylboronic acid and 4-bromo-1H-imidazole, to prepare 4-bromo-1-(4-chlorophenyl)-1H-imidazole. 4-Bromo-1-(4-chlorophenyl)-1H-imidazole (150 mg, 0.0.583 mmol), thiophen-2-ylboronic acid (149 mg, 1.66 mmol), Pd2(dba)3 (27 mg, 0.029 mmol), 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) (28 mg, 0.058 mmol) and Cs2CO3 (475 mg. 1.459 mmol) were then combined in dioxane (5 ml). The reaction mixture was heated under microwave at 90° C. for 16 hours. It was then filtered and washed with ethyl acetate, and the filtrate was concentrated. The crude material was column purified using 15-20% ethyl acetate/hexanes to yield the desired 1-(4-chlorophenyl)-4-(thiophen-2-yl)-1H-imidazole (16 mg, 0.061 mmol, yield 10%) as a reddish solid. The HPLC purity of the final product was 99.35%. LC-MS [M+H] 261 (C13H9ClN2S+H expected 261.02). The 1H-NMR spectra was in accordance with the chemical structure

Workup

  1. filtrationIt was then filtered
  2. washwashed with ethyl acetate
  3. concentrationthe filtrate was concentrated
  4. custompurified

Sources & evidence

ORD record
ord-8998fdb6e9064134bec6a0dbbf2d6a28
Source dataset
uspto-grants-2016_08
Patent number
US09402397B2

Reaction notes

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