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

HRID 870722ノート

反応式

HRID 870722 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 18373917Acetonitrile--water (1/1)溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-43d1c7a61666407986cd97d54bbe0031
出典データセット
uspto-grants-2015_03
特許番号
US08969565B2

反応ノート

読み込み中…