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

HRID 711281

反応式

HRID 711281 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-242b82d0d9dd490294bb460259101abe
出典データセット
uspto-grants-2015_11
特許番号
US09181235B2

関連ノート

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