Potassium Carbonate → 3-(1,1-Dioxidotetrahydro-2H-thiopyran-4-yl)-5-(1H-indazol-5-yl)-1H-indole-7-carboxamide

HRID 387337ノート

反応式

HRID 387337 の反応式
[O:1]=[S:2]1(=[O:29])[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[C:12]([C:26]([NH2:28])=[O:27])[CH:13]=[C:14](B4OC(C)(C)C(C)(C)O4)[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.Br[C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[NH:36][N:35]=[CH:34]2.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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.Cl[Pd]Cl.[Fe+2]>[O:29]=[S:2]1(=[O:1])[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[C:12]([C:26]([NH2:28])=[O:27])[CH:13]=[C:14]([C:31]4[CH:32]=[C:33]5[C:37](=[CH:38][CH:39]=4)[NH:36][N:35]=[CH:34]5)[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 7619295-bromo-1H-indazoleHCID 593327113-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide

生成物 1

HCID 593327043-(1,1-Dioxidotetrahydro-2H-thiopyran-4-yl)-5-(1H-indazol-5-yl)-1H-indole-7-carboxamide収率 24.1%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
100 °C

実験手順

3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (0.085 g, 0.203 mmol) and 5-bromo-1H-indazole (0.048 g, 0.244 mmol, 1.2 eq) was dissolved in a 6:1 solution of 1,4 dioxane/water in a 20 mL microwave reaction vessel. Potassium carbonate (0.128, 0.929 mmol, 4.6 eq) was added and the solution was degassed with Argon. PdCl2(dppf) (0.023 g, 0.032 mmol, 0.16 eq) was added and the reaction was heated in a microwave at 100° C. for 20 min. Solution was passed through a StratoSphere SPE PL-Thiol MP SPE column to remove palladium and purified on Gilson preparative HPLC using Acetonitrile/Water with 0.1% TFA. 0.020 g (24%) product obtained.

後処理

  1. customthe solution was degassed with Argon
  2. customto remove palladium
  3. custompurified on Gilson preparative HPLC

出典と根拠

ORDレコード
ord-0399adc2890d4fd7b3dc6f5f6e23f56a
出典データセット
uspto-grants-2013_02
特許番号
US08372875B2

反応ノート

読み込み中…