Water → 6-[5-(4-Cyano-2-methyl-phenyl)-furan-2-yl]-nicotinonitrile

HRID 853809ノート

反応式

HRID 853809 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1.Br[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[CH3:23].C([O-])(=O)C.[K+].O>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:19]([C:18]1[CH:21]=[CH:22][C:15]([C:5]2[O:1][C:2]([C:6]3[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=3)=[CH:3][CH:4]=2)=[C:16]([CH3:23])[CH:17]=1)#[N:20]

参加物

7

反応物 4

HCID 962WaterHCID 517044Potassium AcetateHCID 27374944-Bromo-3-methylbenzonitrileHCID 111164736-(2-Furyl)nicotinonitrile

生成物 1

HCID 694598846-[5-(4-Cyano-2-methyl-phenyl)-furan-2-yl]-nicotinonitrile収率 40%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

Referring now to Scheme 6, a mixture of 1 (680 mg, 4 mmol), 4-bromo-3-methylbenzonitrile (784 mg, 4 mmol), tetrakis(triphenylphosphine)-palladium(0) (228 mg) and potassium acetate (981.5 mg, 10 mmol) in dry DMF (15 mL) was heated under nitrogen at 120° C. for 16 h. The reaction mixture then poured onto cold-water. The precipitate that formed was collected, dissolved in methylene chloride, and the solution was passed through celite to remove Pd. The solution was evaporated, the solid was filtered and purified to afford 28 (SiO2, hexanes/EtOAc, 1:1), yield 40%, mp 233–234° C. 1H nmr (DMSO-d6); δ 2.61 (s, 3H), 7.25 (d, J=3.6 Hz, 1H), 7.51 (d, J=3.6 Hz, 1H), 7.77 (d, J=8.1 Hz, 1H), 7.82 (s, 1H). 8.03–8.07 (m, 2H), 8.36 (dd, J=8.1, 2.1 Hz, 1H), 9.02 (d, J=2.1 Hz, 1H). 13C nmr; δ 153.2, 152.7, 151.9, 150.2, 140.8, 135.6, 134.8, 132.5, 129.8, 127.3, 118.3, 117.0, 114.4, 110.2, 106.8, 21.2.

後処理

  1. customThe precipitate that formed
  2. customwas collected
  3. dissolutiondissolved in methylene chloride
  4. customto remove Pd
  5. customThe solution was evaporated
  6. filtrationthe solid was filtered
  7. custompurified

出典と根拠

ORDレコード
ord-b7447061b6e34fca99b6a0845c334269
出典データセット
uspto-grants-2007_08
特許番号
US07256203B2

反応ノート

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