Cesium carbonate → HCID 90412745、化合物

HRID 1522048ノート

反応式

HRID 1522048 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[NH:15][C:16]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]4)=[CH:17][C:10]=23)O1.Br[C:33]1[N:38]=[C:37]([NH2:39])[CH:36]=[N:35][CH:34]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[NH2:39][C:37]1[N:38]=[C:33]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[NH:15][C:16]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]4)=[CH:17][C:10]=23)[CH:34]=[N:35][CH:36]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 126931822-Amino-6-bromopyrazineHCID 90413258HCID 90413258、化合物

生成物 1

HCID 90412745HCID 90412745、化合物

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of Example 21A (500 mg, 1.2 mmol), 6-bromopyrazin-2-amine (244 mg, 1.4 mmol), bis(triphenylphosphine)palladium(ii) chloride (82 mg, 0.1 mmol), tricyclohexylphosphine (33 mg, 0.1 mmol) and cesium carbonate (1.2 g, 3.5 mmol) was purged with nitrogen, then anhydrous dioxane (60 ml) was added. The mixture was heated at 100° C. overnight. The reaction was cooled to room temperature and filtrated, and the solid was washed with dichloromethane (200 mL). The filtrate was concentrated and purified by flash chromatography on silica gel using an ISCO Companion eluting with heptanes/ethyl acetate (30%) to provide the title compound. MS (ESI+) m/z 395 (M+H)+.

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltrated
  3. washthe solid was washed with dichloromethane (200 mL)
  4. concentrationThe filtrate was concentrated
  5. custompurified by flash chromatography on silica gel using an ISCO Companion
  6. washeluting with heptanes/ethyl acetate (30%)

出典と根拠

ORDレコード
ord-c816803ab5c44db384979131113b5bcd
出典データセット
uspto-grants-2015_07
特許番号
US09073922B2

反応ノート

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