Cesium carbonate → HCID 66832355、化合物

HRID 1914527

反応式

HRID 1914527 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:9]=1)[C:5]#[N:6].[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.O1CCOCC1>[N:10]1([C:8]2[CH:7]=[C:4]([CH:3]=[C:2]([C:20]3[CH:21]=[CH:22][C:17]([C:16]([F:27])([F:26])[F:15])=[CH:18][CH:19]=3)[N:9]=2)[C:5]#[N:6])[CH2:14][CH2:13][CH2:12][CH2:11]1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 830745802-Chloro-6-(pyrrolidin-1-yl)pyridine-4-carbonitrile

生成物 1

HCID 66832355HCID 66832355、化合物収率 92%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

2-Chloro-6-pyrrolidin-1-yl-isonicotinonitrile (0.18 g, 0.87 mmol), 4-trifluoromethylphenylboronic acid (0.18 g, 0.95 mmol), palladium acetate (3.9 mg, 0.02 mmol), cesium carbonate (0.56 g, 1.73 mmol), and XPhos (17 mg, 0.04 mmol) were combined, placed under a nitrogen atmosphere and dioxane (1.0 mL) was added. The reaction vessel was sealed and heated to 100° C. for 2 hours. The reaction mixture was cooled to rt, filtered through celite, concentrated under reduced pressure and purified by flash column chromatography (0%-80% EtOAc in hexane) to provide the desired product (253 mg, 92%). 1H NMR (400 MHz, CDCl3) δ 8.11 (d, J=8.1 Hz, 2H), 7.70 (d, J=8.2 Hz, 2H), 7.15 (d, J=0.8 Hz, 1H), 6.54 (d, J=0.9 Hz, 1H), 3.55 (bs, 4H), 2.13-1.99 (m, 4H).

後処理

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationfiltered through celite
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash column chromatography (0%-80% EtOAc in hexane)

出典と根拠

ORDレコード
ord-6a7a22c1c5774919996decbdd2dafcfb
出典データセット
uspto-grants-2013_12
特許番号
US08614201B2

関連ノート

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