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

HRID 250512

반응식

HRID 250512 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 178477754HCID 178477754, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f08da7ac3fa24a7584799519aa8d4db6
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863313B2

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