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Cesium carbonate → HCID 89923126、化合物

HRID 921835
ノート
印刷プレビュー

反応式

HRID 921835 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]([CH:18]2[CH2:20][CH2:19]2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:5]2=[N:21][CH:22]=[C:23]([C:24]#[N:25])[N:4]2[N:3]=1.[NH2:26][C:27]1[C:28]([Cl:39])=[CH:29][C:30]([CH2:35][CH2:36][CH:37]=[O:38])=[C:31]([CH:34]=1)[C:32]#[N:33].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].O1CCOCC1>[Cl:39][C:28]1[CH:29]=[C:30]([CH2:35][CH2:36][CH:37]=[O:38])[C:31]([C:32]#[N:33])=[CH:34][C:27]=1[NH:26][C:2]1[N:7]=[C:6]([N:8]([CH:18]2[CH2:20][CH2:19]2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:5]2=[N:21][CH:22]=[C:23]([C:24]#[N:25])[N:4]2[N:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 867084772-Chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrileHCID 89922720HCID 89922720、化合物

生成物 1

HCID 89923126HCID 89923126、化合物収率 19.4%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

2-chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (170 mg, 0.479 mmol), 5-amino-4-chloro-2-(3-oxopropyl)benzonitrile (100 mg, 0.479 mmol, Example 566A), palladium(II) acetate (32.3 mg, 0.144 mmol), DPPF (26.6 mg, 0.048 mmol), Xantphos (27.7 mg, 0.048 mmol), and cesium carbonate (312 mg, 0.958 mmol) were combined in a 50 ml round bottom flask and dioxane (4 mL) was added. The flask was evacuated and backfilled with N2 3×, then heated at 100° C. for 2 h. The reaction was cooled to room temperature and filtered through celite, rinsing with EtOAc. The solvent was removed in vacuo and the material was purified by flash column chromatography (0-80% EtOAc/Hex; 40 g column). 2-((2-chloro-5-cyano-4-(3-oxopropyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (49 mg) was obtained.

後処理

  1. customThe flask was evacuated
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered through celite
  4. washrinsing with EtOAc
  5. customThe solvent was removed in vacuo
  6. customthe material was purified by flash column chromatography (0-80% EtOAc/Hex; 40 g column)

出典と根拠

ORDレコード
ord-98a7c2e2acdd4becb7a6eb8dc9ba8ebc
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09273057B2

反応ノート

読み込み中…

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