Potassium Phosphate, Tribasic → HCID 58268026, 화합물

HRID 244707노트

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HRID 244707 반응식
[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

참가 물질

7

반응물 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

생성물 1

HCID 58268026HCID 58268026, 화합물수율 30.2%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매2회

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8f347ca9bab246fdaa86f144aeff3e9a
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658635B2

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