Cesium carbonate → 4-(furan-2-yl)-1-phenyl-1H-pyrazole

HRID 705009

반응식

HRID 705009 반응식
Br[C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1.[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C(CO)=CC=CC=1.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:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 7868114-Bromo-1-phenyl-1H-pyrazoleHCID 2734357Furan-2-boronic acid

생성물 1

HCID 863036594-(furan-2-yl)-1-phenyl-1H-pyrazole수율 16.7%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 69942-Methylbenzyl alcohol용매

반응 조건

온도
80 °C

실험 절차

4-bromo-1-phenyl-1H-pyrazole (140 mg, 0.627 mmol), furan-2-ylboronic acid (88.2 mg, 0.941 mmol), Pd(PPh3)4 (70 mg, 0.062 mmol), and Cs2CO3 (400 mg, 1.254 mmol) were combined in toluene-methanol (1:1) (2 ml). The reaction mixture was heated under microwave at 80° C. for 60 minutes. The reaction mixture was then filtered and washed with toluene-ethanol (5 ml), and the filtrate was concentrated. The crude product was column purified using 15-20% ethyl acetate/hexanes, and was then further purified by preparative HPLC to yield the desired 4-(furan-2-yl)-1-phenyl-1H-pyrazole (22 mg, 0.10 mmol 16.7%). The HPLC purity of the final product was 99.72%. LC-MS [M+H] 211 (C13H10N2O+H expected 211.08). The 1H-NMR spectra was in accordance with the chemical structure.

후처리

  1. filtrationThe reaction mixture was then filtered
  2. washwashed with toluene-ethanol (5 ml)
  3. concentrationthe filtrate was concentrated
  4. custompurified
  5. customwas then further purified by preparative HPLC

출처 및 근거

ORD 기록
ord-8e408364340b4affbd50f16d2d970f08
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173401B2

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