Cesium carbonate → 6-(1H-indazol-4-yl)-1-methyl-N-(4-(methylsulfonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-amine

HRID 241958ノート

反応式

HRID 241958 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[N:11][NH:12]3)[N:5]=[C:4]2[N:17]([CH3:20])[N:18]=[CH:19][C:3]=12.Cl.[CH3:22][S:23]([C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(OC(=O)C)C.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH:12]1[C:13]2[C:9](=[C:8]([C:6]3[CH:7]=[C:2]([NH:30][C:29]4[CH:28]=[CH:27][C:26]([S:23]([CH3:22])(=[O:25])=[O:24])=[CH:32][CH:31]=4)[C:3]4[CH:19]=[N:18][N:17]([CH3:20])[C:4]=4[N:5]=3)[CH:16]=[CH:15][CH:14]=2)[CH:10]=[N:11]1

参加物

8

反応物 3

HCID 10796Cesium carbonateHCID 27351804-(Methylsulfonyl)aniline hydrochlorideHCID 580832344-Chloro-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine

生成物 1

HCID 462203326-(1H-indazol-4-yl)-1-methyl-N-(4-(methylsulfonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-amine収率 17.1%

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒2 回HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A solution of 4-chloro-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine 7 (0.04 g, 0.14 mmol) in dioxane was treated with 4-methylsulphonylaniline hydrochloride (0.058 g, 0.28 mmol) in the presence of (tris(dibenzylidene acetone)dipalladium(0), Pd2(dba)3 (0.13 g, 0.014 mmol), XANPHOS (0.016 g, 0.028 mmol) and cesium carbonate (0.18 g, 0.56 mmol) and the reaction mixture were heated overnight at 100° C. The reaction mixture was diluted with ethylacetate and water. The aqueous portions were extracted with ethyl acetate and the organic portions pooled and dried over anhydrous sodium sulfate. The solvent were removed and the crude material purified (Biotage) to obtain 10 mg of 104. 1H NMR (400 MHz, MeOD) δ 8.69 (s, 1H), 8.12 (s, 1H), 7.97 (d, J=8.7, 2H), 7.78-7.55 (m, 4H), 7.59-7.44 (m, 2H), 4.17 (s, 3H), 3.35 (s, 1H), 3.14 (s, 3H). MS (ESI) m/z 419.2 (M+1)+

後処理

  1. extractionThe aqueous portions were extracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent were removed
  4. customthe crude material purified (Biotage)

出典と根拠

ORDレコード
ord-46cafb83327844f28b5a43385329f183
出典データセット
uspto-grants-2014_02
特許番号
US08653098B2

反応ノート

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