Cesium carbonate → N-(4-(4-methyl-1H-imidazol-1-yl)benzyl)biphenyl-4-carboxamide

HRID 711281

Reaction equation

HRID 711281 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:24][C:25]1[N:26]=[CH:27][NH:28][CH:29]=1.N1C=CC=CC=1C(=O)CC(C1C=CC=CN=1)=O.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I.CN(C=O)C>[CH3:24][C:25]1[N:26]=[CH:27][N:28]([C:2]2[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:12][CH:11]=3)=[O:9])=[CH:4][CH:3]=2)[CH:29]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27284941,3-Di(2-pyridyl)-1,3-propanedioneHCID 67208625N-(4-bromobenzyl)biphenyl-4-carboxamideHCID 178418800HCID 178418800, compound

Product 1

HCID 66632643N-(4-(4-methyl-1H-imidazol-1-yl)benzyl)biphenyl-4-carboxamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a reaction vessel was added N-(4-bromobenzyl)biphenyl-4-carboxamide 10-3 (50 mg, 0.14 mmol), 4-methyl-1H-imidazole 11-1 (17 mg, 0.2 mmol), CuI (9 mg, 0.05 mmol), 1,3-di(pyridin-2-yl)propane-1,3-dione (15 mg, 0.07 mmol), Cs2CO3 (89 mg, 0.27 mmol) and DMF (0.7 mL). The reaction was flushed with nitrogen and stirred at 110° C. overnight. After cooling to room temperature, the reaction was diluted into ethyl acetate. The salt was removed by filtration and filtrate was dried. The residue was purified by HPLC to give N-(4-(4-methyl-1H-imidazol-1-yl)benzyl)biphenyl-4-carboxamide 92. MS m/z 368.2 (M+1). 1H NMR 400 MHz (DMSO-d6) δ 9.16 (t, 1H), 8.17 (s, 1H), 8.02 (d, 2H), 7.81 (d, 2H), 7.75 (d, 2H), 7.58 (d, 2H), 7.52-7.40 (m, 6H), 4.54 (d, 2H), 2.17 (s, 3H).

Workup

  1. customThe reaction was flushed with nitrogen
  2. temperatureAfter cooling to room temperature
  3. additionthe reaction was diluted into ethyl acetate
  4. customThe salt was removed by filtration and filtrate
  5. customwas dried
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-242b82d0d9dd490294bb460259101abe
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Linked notes

Loading…