Cesium carbonate → (4-((5-(4-hydroxyphenyl)-1H-pyrazol-1-yl)methyl)phenyl)(pyrrolidin-1-yl)methanone

HRID 1399810ノート

反応式

HRID 1399810 の反応式
Br[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][CH:3]=1.[OH:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[N:6]([CH2:7][C:8]3[CH:13]=[CH:12][C:11]([C:14]([N:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)=[O:15])=[CH:10][CH:9]=3)[N:5]=[CH:4][CH:3]=2)=[CH:24][CH:23]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 27343604-Hydroxyphenylboronic acidHCID 86729227(4-((5-bromo-1H-pyrazol-1-yl)methyl)phenyl)(pyrrolidin-1-yl)methanone

生成物 1

HCID 136341374(4-((5-(4-hydroxyphenyl)-1H-pyrazol-1-yl)methyl)phenyl)(pyrrolidin-1-yl)methanone収率 71.1%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
140 °C

実験手順

To a solution of (4-((5-bromo-1H-pyrazol-1-yl)methyl)phenyl)(pyrrolidin-1-yl)methanone (231 mg, 0.7 mmol) in dioxane:water (5:1, 25 ml) was added (4-hydroxyphenyl)boronic acid (207 mg, 1.5 mmol), Cs2CO3 (487 mg, 1.5 mmol) and Pd(dppf)Cl2 (86 mg) and the mixture purged with nitrogen. The mixture was then stirred at 140° C. under microwave mediated heating irradiation for 40 min. The mixture was diluted with water, extracted with ethyl acetate three times and the organic layer dried over Na2SO4 before concentration. The crude product was then purified by column chromatography to yield the desired product (173 mg, yield 70%). LCMS (m/z): 348.2 [M+H]+

後処理

  1. customthe mixture purged with nitrogen
  2. temperaturemediated heating
  3. customirradiation for 40 min
  4. additionThe mixture was diluted with water
  5. extractionextracted with ethyl acetate three times
  6. dry with materialthe organic layer dried over Na2SO4 before concentration
  7. customThe crude product was then purified by column chromatography

出典と根拠

ORDレコード
ord-6aebc4b4fb1c4d0780f3301a3a41f95c
出典データセット
uspto-grants-2014_12
特許番号
US08906900B2

反応ノート

読み込み中…