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Potassium Carbonate → (4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(4'-dimethylamino-biphenyl-3-yl)methanone

HRID 916770
ノート
印刷プレビュー

反応式

HRID 916770 の反応式
[Cl:1][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15](I)[CH:14]=3)=[O:12])=[CH:9][N:8]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:25][N:26]([CH3:36])[C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CCOC(C)=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>[Cl:1][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:14]=[C:15]([C:30]4[CH:31]=[CH:32][C:27]([N:26]([CH3:36])[CH3:25])=[CH:28][CH:29]=4)[CH:16]=[CH:17][CH:18]=3)=[O:12])=[CH:9][N:8]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:4]=2[N:5]=[CH:6][N:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 27343444-(Dimethylamino)phenylboronic acidHCID 86760548(4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-iodo-phenyl)-methanone

生成物 1

HCID 86760550(4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(4'-dimethylamino-biphenyl-3-yl)methanone収率 47%

試薬・触媒・溶媒 4

HCID 178418476
HCID 178418476、化合物
触媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

実験手順

A solution of (4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-iodo-phenyl)-methanone (100 mg, 0.22 mmol), 4-(dimethylamino)Phenyl boronic acid (42.9 mg, 0.26 mmol), PdCl2(PPh3)2 (7.7 mg, 0.011 mmol), and K2CO3 (45.6 mg, 0.33 mmol) in 1,4-dioxane (3 mL) and water (0.5 mL) was heated to 90° C. After 24 h the reaction was diluted with EtOAc and filtered through celite. The filtrate was washed with water, dried over Na2SO4, and concentrated. Purification by flash column chromatography (hexanes/ethyl acetate 8:2) afforded the title compound as a white solid (46 mg, 47%). MS: 445.1/447.1 (MH+); HPLC Rf: 8.05 min. (HPLC method 4).

後処理

  1. filtrationfiltered through celite
  2. washThe filtrate was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (hexanes/ethyl acetate 8:2)

出典と根拠

ORDレコード
ord-f3056eff86ce46bc949883f25a951ed7
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07271262B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート