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Water → 2-(4-Fluorophenyl)-8-vinylimidazo[1,2-a]pyrazine

HRID 2233079
ノート
印刷プレビュー

反応式

HRID 2233079 の反応式
Cl[C:2]1[C:3]2[N:4]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][N:7]=1.O.C(=O)([O-])[O-].[Na+].[Na+].F[B-](F)(F)F.[C:30](P(C(C)(C)C)C(C)(C)C)(C)(C)[CH3:31]>O1CCOCC1.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]>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:3]3[C:2]([CH:30]=[CH2:31])=[N:7][CH:6]=[CH:5][N:4]3[CH:8]=2)=[CH:12][CH:13]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 44558591Tri-t-butylphosphine fluoroborateHCID 574387418-Chloro-2-(4-fluorophenyl)imidazo[1,2-A]pyrazine

生成物 1

HCID 574387402-(4-Fluorophenyl)-8-vinylimidazo[1,2-a]pyrazine収率 642.6%

試薬・触媒・溶媒 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

To a mixture of 8-chloro-2-(4-fluorophenyl)-imidazo[1,2-a]pyrazine (Example #6, Step A, 3.96 g, 16 mmol) in dioxane (80 mL) was added water (15.4 mL), sodium carbonate (EM Science, 5.08 g, 48 mmol), tri-t-butylphosphine tetrafluoroborate (Strem, 0.46 g, 1.6 mmol), and tris(dibenzylideneacetone)dipalladium(0) (0.73 g, 0.8 mmol). The reaction was degassed with nitrogen and then vinylboronic acid pinacolester (5.44 mL, 32 mmol) was added. The mixture was heated to about 95° C. for about 16 h. The reaction was cooled, EtOAc was added (250 mL), and the mixture was washed with water. The organic layer was dried over sodium sulfate, filtered, and evaporated. The residue was purified by FCC (33%-50% EtOAc/heptane). The residue was triturated with heptane and filtered to yield the title compound as a brown solid (2.46 g, 62%): LC/MS (Table 1, Method b) Rt=2.74 min; MS m/z: 240.3 (M+H)+.

後処理

  1. customThe reaction was degassed with nitrogen
  2. additionvinylboronic acid pinacolester (5.44 mL, 32 mmol) was added
  3. temperatureThe reaction was cooled
  4. additionEtOAc was added (250 mL)
  5. washthe mixture was washed with water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by FCC (33%-50% EtOAc/heptane)
  10. customThe residue was triturated with heptane
  11. filtrationfiltered

出典と根拠

ORDレコード
ord-c81084fa5c8e49cd97f9962520398057
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07709468B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート