Water → 4-(4-Methoxyphenyl)-1-(3-methylbutyl)-1H-pyrazole

HRID 250512

反応式

HRID 250512 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH3:10][CH:11]([CH3:28])[CH2:12][CH2:13][N:14]1[CH:18]=[C:17](B2OC(C)(C)C(C)(C)O2)[CH:16]=[N:15]1.C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:17]2[CH:16]=[N:15][N:14]([CH2:13][CH2:12][CH:11]([CH3:28])[CH3:10])[CH:18]=2)=[CH:3][CH:4]=1

参加物

7

反応物 4

HCID 962WaterHCID 77304-BromoanisoleHCID 11430Potassium CarbonateHCID 27598311-(3-Methylbutyl)-1H-pyrazole-4-boronic acid pinacol ester

生成物 1

HCID 112880284-(4-Methoxyphenyl)-1-(3-methylbutyl)-1H-pyrazole収率 127.4%

試薬・触媒・溶媒 2

HCID 178477754HCID 178477754、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To p-bromoanisole (0.25 g, 1.33 mmol) was added a solution of 1-(3-methylbutyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.41 g, 1.55 mmol) in tetrahydrofuran (10 ml), potassium carbonate (0.29 g, 2.1 mmol) and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (12 mg, 0.023 mmol) and the mixture refluxed under nitrogen for 17 h. Water (50 ml) was added to the reaction mixture and stirring continued at RT for 15 min followed by extraction with ether (2×50 ml), drying (MgSO4) and evaporation of the ether extract to give a brown oil (0.414 g). Purification by column chromatography (silica gel, 100% chloroform) afforded 4-(4-methoxyphenyl)-1-(3-methylbutyl)-1H-pyrazole (12) as a waxy pale yellow solid (37 mg, 11%). 1H nmr (CDCl3, 300 MHz) 0.97, d (6.6 Hz), 2×Me; 1.64, sept (6.6 Hz), H3″; 1.80, dt (7.2 Hz), H2″; 3.82, s, OMe; 4.15, t (7.5 Hz), H1″; 6.90, d (8.7 Hz), H3′,5′; 7.39, d (8.7 Hz), H2′,6′; 7.54, s, H3 or H5; 7.69, s, H5 or H3. ESI (+ve) MS m/z 245 (M+H, 100%).

後処理

  1. temperaturethe mixture refluxed under nitrogen for 17 h
  2. extractionfollowed by extraction with ether (2×50 ml)
  3. customdrying
  4. custom(MgSO4) and evaporation of the ether
  5. extractionextract

出典と根拠

ORDレコード
ord-f08da7ac3fa24a7584799519aa8d4db6
出典データセット
uspto-grants-2011_01
特許番号
US07863313B2

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