Cesium carbonate → (+/-)-2'-(1-Cyano-2,2-dipyridin-3-ylethyl)-1,1'-biphenyl-3-carbonitrile

HRID 1686080노트

반응식

HRID 1686080 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH:11]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[C:9]#[N:10].[C:24]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)#[N:25].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O>[C:9]([CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:30]1[CH:29]=[CH:28][CH:27]=[C:26]([C:24]#[N:25])[CH:31]=1)[CH:11]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)#[N:10]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 27343253-Cyanophenylboronic acidHCID 672655872-(2-Bromophenyl)-3,3-dipyridin-3-ylpropanenitrile

생성물 1

HCID 57867552(+/-)-2'-(1-Cyano-2,2-dipyridin-3-ylethyl)-1,1'-biphenyl-3-carbonitrile

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

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온도
160 °C

실험 절차

A mixture of 2-(2-bromophenyl)-3,3-dipyridin-3-ylpropanenitrile (0.050 g, 0.137 mmol), 3-cyanophenylboronic acid (0.030 g, 0.206 mmol), cesium carbonate (0.045 g, 0.137 mmol) and Pd(dppf)2 (0.100 g, 0.137 mmol) in THF (0.75 mL) and water (0.75 mL) at −78° C. was heated to 160° C. in microwave for 15 min. The reaction was diluted with water and extracted with CH2Cl2. The combined organic layer was dried, filtered, and concentrated. The residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2) to give (±)-2′-(1-cyano-2,2-dipyridin-3-ylethyl)-1,1′-biphenyl-3-carbonitrile. 1H-NMR (500 MHz, CDCl3) δ 8.57 (d, 1H, J=3.9), 8.45 (d, 1H, J=4.2), 8.42 (s, 1H), 7.88 (s, 1H), 7.71 (m, 1H), 7.66-7.56 (m, 3H), 7.51 (td, 1H, J=7.5, 1.2), 7.41 (td, 1H, J=7.6, 1.3), 7.34-7.32 (m, 2H), 7.18-7.07 (m, 3H), 7.00 (d, 1H, J=7.8), 4.57 (d, 1H, J=10.0), 4.33 (d, 1H, J=9.8). LRMS m/z (M+H) Calcd: 387.1604, found: 387.1592.

후처리

  1. extractionextracted with CH2Cl2
  2. customThe combined organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-b1118cc6bec9424fbfe6b561c645db56
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148535B2

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