Cesium carbonate → (1-(3-bromo-4-methoxyphenyl)-1H-pyrazol-3-yl)methanol

HRID 1027274

反応式

HRID 1027274 の反応式
N1C=CC=CC=1C1NC2C=CC=CC=2N=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:22]1[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[N:23]1.[Br:29][C:30]1[CH:35]=[C:34](I)[CH:33]=[CH:32][C:31]=1[O:37][CH3:38]>CCOC(C)=O.[Cu]I.CN(C=O)C>[Br:29][C:30]1[CH:35]=[C:34]([N:22]2[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[N:23]2)[CH:33]=[CH:32][C:31]=1[O:37][CH3:38]

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 708212-(2'-Pyridyl)benzimidazoleHCID 33767792-Bromo-4-iodoanisoleHCID 178519763HCID 178519763、化合物

生成物 1

HCID 86710689(1-(3-bromo-4-methoxyphenyl)-1H-pyrazol-3-yl)methanol収率 77.9%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a 100 mL round bottom flask was added copper (I) iodide (30.4 mg, 0.16 mmol), 2-(2-pyridyl)benzimidazole (31.2 mg, 0.16 mmol), cesium carbonate (625 mg, 1.92 mmol) and DMF (5.3 mL). The reaction mixture was heated to 60° C. for 1 h then (1H-pyrazol-3-yl)methanol (235 mg, 2.40 mmol) and 2-bromo-4-iodo-1-methoxybenzene (500 mg, 1.60 mmol) were added and the mixture was heated at 100° C. for 18 hours. The reaction was cooled, diluted with EtOAc and filtered through celite. The filtrate was concentrated in vacuo and purified by silica gel chromatography (0-100% EtOAc in Hepane) to afford (1-(3-bromo-4-methoxyphenyl)-1H-pyrazol-3-yl)methanol (353 mg) MS [M+2H+]=285.0.

後処理

  1. temperaturethe mixture was heated at 100° C. for 18 hours
  2. temperatureThe reaction was cooled
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by silica gel chromatography (0-100% EtOAc in Hepane)

出典と根拠

ORDレコード
ord-defd10b236444fda9f9906956cc2d1e5
出典データセット
uspto-grants-2014_05
特許番号
US08729263B2

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