1,4-Dioxane → 1-(2-(2-tert-Butylphenoxy)-5-cyanopyridin-3-yl)-3-(4-tert-butylphenyl)urea

HRID 132606

反応式

HRID 132606 の反応式
[NH2:1][C:2]1[C:3]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#[N:8].[Cu][C:22]#[N:23].[O:24]1[CH2:29]COCC1>[C-]#N.C([N+](CC)(CC)CC)C.CCOCC.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].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][C:3]1[C:2]([NH:1][C:29]([NH:23][C:22]2[CH:14]=[CH:13][C:12]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11][CH:16]=2)=[O:24])=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1)([CH3:20])([CH3:19])[CH3:18]

参加物

8

反応物 3

HCID 312751,4-DioxaneHCID 685300435-Amino-6-(2-tert-butylphenoxy)nicotinonitrileHCID 178418546HCID 178418546、化合物

生成物 1

HCID 115540381-(2-(2-tert-Butylphenoxy)-5-cyanopyridin-3-yl)-3-(4-tert-butylphenyl)urea

試薬・触媒・溶媒 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 3014735Tetraethylammonium cyanide触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
105 °C

実験手順

5-Amino-6-(2-tert-butylphenoxy)nicotinonitrile: A mixture of 63c (676 mg, 2.1 mmol), copper (1) cyanide (755 mg, 8.4 mmol), tris(dibenzilideneacetone)dipalladium(0) (77 mg, 0.08 mmol), bis(diphenylphosphino)ferrocene (187 mg, 0.34 mmol) and tetraethylammonium cyanide (330 mg, 2.1 mmol) in dioxane (11 mL) was heated at 105° C. overnight. The mixture was cooled to rt, diluted with ether (50 mL), filtered through Celite® and silica (3 g) and concentrated to give a brown solid (883 mg). The solid was purified by SiO2 chromatography (40 g) to afford 63d (472 mg. 84% yield) as a yellow solid; HPLC purity 95%, 3.37 min (Method A); [M+H]+=268.15; 1H NMR (CDCl3) δ ppm: 1.35 (s, 9 H) 4.26 (s, 2 H) 6.95 (d, J=7.70 Hz, 1 H) 7.15 (s, 1 H) 7.20 (t, J=7.70 Hz, 1 H) 7.25 (t, J=7.42 Hz, 1 H) 7.47 (d, J=7.70 Hz, 1 H) 7.82 (s, 1 H); 13C NMR (CDCl3) δ ppm: 154.22, 151.27, 141.40, 139.75, 131.98, 127.57, 127.03, 125.53, 123.53, 121.69, 117.38, 104.08, 34.60, 30.47.

後処理

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through Celite® and silica (3 g)
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-901db812d251499d9e832bd475385333
出典データセット
uspto-grants-2008_06
特許番号
US07388021B2

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