Cesium carbonate → tert-Butyl 4-(5-(furan-3-yl)-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate

HRID 1045710ノート

反応式

HRID 1045710 の反応式
Br[C:2]1[N:7]2[CH:8]=[N:9][N:10]=[C:6]2[C:5]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[N:4][CH:3]=1.[O:24]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25]1.C([O-])([O-])=O.[Cs+].[Cs+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[O:24]1[CH:28]=[CH:27][C:26]([C:2]2[N:7]3[CH:8]=[N:9][N:10]=[C:6]3[C:5]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[N:4][CH:3]=2)=[CH:25]1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 2734358Furan-3-boronic acidHCID 58447004Tert-butyl 4-(5-bromo-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate

生成物 1

HCID 58447023tert-Butyl 4-(5-(furan-3-yl)-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate収率 97.3%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A 50 mL round bottom flask was charged with tert-butyl 4-(5-bromo-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate (800 mg, 2.08 mmol), furan-3-ylboronic acid (349 mg, 3.12 mmol), Pd(PPh3)4 (240 mg, 0.312 mmol), Cs2CO3 (1.00 g, 3.12 mmol), 1,4-dioxane (11 mL) and water (4 mL). The resulting mixture was heated under N2 at 100° C. overnight. Work-up: the reaction mixture was filtered. The filter cake was washed with EtOAc (10 mL) and the filtrate was extracted with more EtOAc (10 mL×3). The combined organic solutions were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 2% methanol in dichloromethane, to afford 0.75 g (97%) of the product as a yellow solid. MS m/z: 371 (M+H+).

後処理

  1. filtrationthe reaction mixture was filtered
  2. washThe filter cake was washed with EtOAc (10 mL)
  3. extractionthe filtrate was extracted with more EtOAc (10 mL×3)
  4. washThe combined organic solutions were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel with 2% methanol in dichloromethane

出典と根拠

ORDレコード
ord-8463c6b0fd0b4ab38940c8e72f8116c7
出典データセット
uspto-grants-2013_10
特許番号
US08569300B2

反応ノート

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