Cesium carbonate → HCID 44553618、化合物

HRID 714394ノート

反応式

HRID 714394 の反応式
[CH2:1]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][N:13]=[C:12](Cl)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([CH:24]2[CH2:29][CH2:28][NH:27][C:26](=[O:30])[CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([NH:8][C:9]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([N:27]2[CH2:28][CH2:29][CH:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:25][C:26]2=[O:30])[CH:11]=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 3

HCID 10796Cesium carbonateHCID 15115857N-benzyl-2-chloropyridine-4-carboxamideHCID 198177874-Phenyl-2-piperidinone

生成物 1

HCID 44553618HCID 44553618、化合物収率 77.8%

試薬・触媒・溶媒 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

A degassed mixture of N-benzyl-2-chloroisonicotinamide (0.05 g, 0.20 mmol), 4-phenylpiperidin-2-one (0.04 g, 0.22 mmol), cesium carbonate (0.20 g, 0.61 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.005 g, 0.008 mmol), tris(dibenzylideneacetone)dipalladium (0.004 g, 0.004 mmol) in N,N-dimethylformamide (3.0 mL) was heated at 90° C. for 18 hours and cooled to ambient temperature. The resulting solution was diluted with ethyl acetate (30 mL), washed with water (20 mL) and brine (20 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give 2-oxo-4-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4′-carboxylic acid benzylamide as a colorless solid (0.06 g, 77%): mp 55-60° C.; 1H NMR (300 MHz, CDCl3) δ 8.46 (d, J=5.1 Hz, 1H), 8.09 (s, 1H), 7.50 (d, J=5.1 Hz, 1H), 7.40-7.16 (m, 11H), 4.59-4.46 (m, 2H), 4.09-3.84 (m, 2H), 3.24-3.09 (m, 1H), 2.79 (dd, J=17.5, 5.3 Hz, 1H), 2.61 (dd, J=17.5, 11.2 Hz, 1H), 2.26-2.22 (m, 1H), 2.13-1.95 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 170.6, 165.1, 154.8, 148.7, 143.2, 142.9, 137.8, 128.9, 128.7, 128.1, 127.6, 127.0, 126.5, 119.0, 117.8, 47.4, 44.1, 40.8, 38.6, 30.3; MS (ES+) m/z 386.5 (M+1).

後処理

  1. temperaturecooled to ambient temperature
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-1372cf2f71914357939a4482a472a825
出典データセット
uspto-grants-2015_11
特許番号
US09187426B2

反応ノート

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