3-(Tributylstannyl)pyridine → 2-(4-Fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)-5-(3-pyridyl)imidazo-[4,5-b]pyridine

HRID 2181416

反応式

HRID 2181416 の反応式
Cl[C:2]1[N:7]=[C:6]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[N:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[N:12]=3)[C:5]2=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)CCC>C1(C)C(C)=CC=CC=1.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>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:9]2[N:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[N:12]=3)[C:5]3[C:6]([N:8]=2)=[N:7][C:2]([C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)=[CH:3][CH:4]=3)=[CH:24][CH:25]=1

参加物

5

反応物 2

HCID 34838483-(Tributylstannyl)pyridineHCID 224861525-Chloro-2-(4-fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)imidazo[4,5-b]pyridine

生成物 1

HCID 224861392-(4-Fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)-5-(3-pyridyl)imidazo-[4,5-b]pyridine収率 58.8%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 7237O-Xylene溶媒

実験手順

5-Chloro-2-(4-fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)imidazo[4,5-b]pyridine (2 g 4.9 mmol), 3-tributylstannylpyridine (3.6 g 9.8 mmol) and PdCl2(PPh3)2 (340 mg 0.48 mmol) are heated in xylene (50 ml) for 3 h at 150° C. under argon. The reaction mixture is filtered at 60° C. and chromatographed over SiO2 (acetone/hexanes 3/7 to 6/4) to yield pale yellow crystals (1.3 g). Recrystallisation from THF/hexanes renders the title compound as colorless crystals (985 mg 45%).

後処理

  1. filtrationThe reaction mixture is filtered at 60° C.
  2. customchromatographed over SiO2 (acetone/hexanes 3/7 to 6/4)

出典と根拠

ORDレコード
ord-e3f7109038d549de980b1b4a6ea44447
出典データセット
uspto-grants-2005_05
特許番号
US06891039B2

関連ノート

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