Potassium Carbonate → (3-Cyclopent-1-enyl-imidazo[1,2-b]pyridazin-6-yl)-[2-(2-ethoxy-phenyl)-ethyl]-amine

HRID 870722노트

반응식

HRID 870722 반응식
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH3:22])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[C:23]1(B2OC(C)(C)C(C)(C)O2)[CH2:27][CH2:26][CH2:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:23]1([C:2]2[N:6]3[N:7]=[C:8]([NH:11][CH2:12][CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[O:20][CH2:21][CH3:22])[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)[CH2:27][CH2:26][CH2:25][CH:24]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 154866112-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86696426(3-Bromo-imidazo[1,2-b]pyridazin-6-yl)-[2-(2-ethoxy-phenyl)-ethyl]-amine

생성물 1

HCID 86696427(3-Cyclopent-1-enyl-imidazo[1,2-b]pyridazin-6-yl)-[2-(2-ethoxy-phenyl)-ethyl]-amine수율 68.9%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 18373917Acetonitrile--water (1/1)용매

반응 조건

온도
150 °C

실험 절차

A mixture of (3-bromo-imidazo[1,2-b]pyridazin-6-yl)-[2-(2-ethoxy-phenyl)-ethyl]-amine (90 mg, 0.25 mmol), 2-cyclopent-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (97 mg, 0.5 mmol), K2CO3 (104 mg, 0.75 mmol) and dichlorobis(triphenylphosphine)palladium(II) (8.8 mg, 0.013 mmol) in MeCN/water (2.8 ml/0.7 ml) was heated in a microwave at 150° C. for 15 min. The water layer was removed and the organic layer was concentrated. The residue was subjected to ISCO. The product was further purified by preparative to give the titled compound (60 mg).

후처리

  1. customThe water layer was removed
  2. concentrationthe organic layer was concentrated
  3. customThe product was further purified by preparative

출처 및 근거

ORD 기록
ord-43d1c7a61666407986cd97d54bbe0031
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969565B2

반응 노트

불러오는 중…