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

HRID 711281

반응식

HRID 711281 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-242b82d0d9dd490294bb460259101abe
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181235B2

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