Biphenyl → 5-(2,4-dichlorophenyl)-3,6-diethyl-N-(1-propyl-1H-imidazol-2-yl)pyrazin-2-amine

HRID 1612316ノート

反応式

HRID 1612316 の反応式
Br[C:2]1[C:7]([CH2:8][CH3:9])=[N:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[C:4]([CH2:18][CH3:19])[N:3]=1.[CH2:20]([N:23]1[CH:27]=[CH:26][N:25]=[C:24]1[NH2:28])[CH2:21][CH3:22].C1(C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>O1CCOCC1.C([O-])(O)=O.[Na+].[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[C:5]1[N:6]=[C:7]([CH2:8][CH3:9])[C:2]([NH:28][C:24]2[N:23]([CH2:20][CH2:21][CH3:22])[CH:27]=[CH:26][N:25]=2)=[N:3][C:4]=1[CH2:18][CH3:19]

参加物

8

反応物 4

HCID 7095BiphenylHCID 221474372-Bromo-5-(2,4-dichlorophenyl)-3,6-diethylpyrazineHCID 221475261-propyl-1H-imidazol-2-amineHCID 23676156Sodium t-butoxide

生成物 1

HCID 103097425-(2,4-dichlorophenyl)-3,6-diethyl-N-(1-propyl-1H-imidazol-2-yl)pyrazin-2-amine収率 27.2%

試薬・触媒・溶媒 3

HCID 9832798Tris(dibenzylideneacetone) dipalladium触媒HCID 312751,4-Dioxane溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
110 °C

実験手順

A mixture of 2-bromo-5-(2,4-dichlorophenyl)-3,6-diethylpyrazine (0.25 g, 0.69 mmol), 1-propyl-1H-imidazol-2-amine (0.15 g, 1.2 mmol), tris(dibenzylideneacetone) dipalladium (0.032 g, 0.032 mmol), 2-dicyclohexylphosphino)biphenyl (0.037 g, 0.12 mmol), and sodium tert-butoxide (0.093 g, 0.97 mmol) in dioxane (2.0 mL) was heated at 110° C. for 21 h. After cooling to rt, the reaction was diluted with saturated aqueous NaHCO3 and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40M) with (Biotage, 40S) with heptanes/EtOAc (3:1) to give 0.076 g (27%) of dark yellow oil: 1H NMR (400 MHz, CDCl3) δ 12.86, 7.47, 7.31, 6.70, 6.55, 3.94, 2.97, 2.48, 2.97, 2.48, 1.84, 1.30, 1.21, 0.98; IR (liq.) 2968, 2934, 1599, 1556, 1549, 1509, 1460, 1422, 1402, 1384, 1373, 1302, 1174, 1102, 712 cm−1; HRMS (FAB) calcd for C20H23Cl2N5+H 404.1408, found 404.1416.

後処理

  1. temperatureAfter cooling to rt
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (Biotage, 40M) with (Biotage, 40S) with heptanes/EtOAc (3:1)

出典と根拠

ORDレコード
ord-f8a4a31054d64ccc9b31be0e491e6677
出典データセット
uspto-grants-2006_01
特許番号
US06992087B2

反応ノート

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