Potassium Phosphate, Tribasic → HCID 58268026、化合物

HRID 1615996ノート

反応式

HRID 1615996 の反応式
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[C:16](B4OC(C)(C)CC(C)(C)O4)[CH:15]=[C:14]([NH2:29])[C:13]=3[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:31]1[CH:32]=[C:33]2[CH:39]=[N:38][N:37]([S:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)(=[O:42])=[O:41])[C:34]2=[N:35][CH:36]=1.P([O-])([O-])([O-])=O.[K+].[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]>[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[C:16]([C:31]4[CH:32]=[C:33]5[CH:39]=[N:38][N:37]([S:40]([C:43]6[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=6)(=[O:41])=[O:42])[C:34]5=[N:35][CH:36]=4)[CH:15]=[C:14]([NH2:29])[C:13]=3[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 583564165-bromo-1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridineHCID 670292681-(Phenylsulfonyl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-1H-indazol-4-amine

生成物 1

HCID 58268026HCID 58268026、化合物収率 30.2%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
100 °C

実験手順

1-(Phenylsulfonyl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-1H-indazol-4-amine (1.5 g, 3.63 mmol), 5-bromo-1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridine (1.350 g, 3.99 mmol), Pd(dppf)Cl2 (0.531 g, 0.726 mmol) and tripotassium phosphate (2.311 g, 10.89 mmol) were divided between 2 microwave vials and dissolved in 1,4-dioxane (18 mL) and Water (6 mL); 9 ml dioxane and 3 ml water in each. Each vial was heated to 100° C. for 10 min in the microwave. Solvent was removed in vacuo and the residue was partitioned between DCM (100 ml) and water (100 ml). The organic layer was collected using a hydrophobic frit and the solvent was removed in vacuo. The residue was taken up in DCM (4 ml) and added to the top of 2×70 g silica SPE cartridges. These were subsequently eluted with 0-100% EtOAc/DCM over 40 mins. The product-containing fractions were combined to give the title compound as a pale yellow solid (581 mg).

後処理

  1. customSolvent was removed in vacuo
  2. customthe residue was partitioned between DCM (100 ml) and water (100 ml)
  3. customThe organic layer was collected
  4. customthe solvent was removed in vacuo
  5. additionadded to the top of 2×70 g silica SPE cartridges
  6. washThese were subsequently eluted with 0-100% EtOAc/DCM over 40 mins

出典と根拠

ORDレコード
ord-823c3dfe6d794a2e83bd288c7e9d9c80
出典データセット
uspto-grants-2014_07
特許番号
US08765743B2

反応ノート

読み込み中…