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Potassium Phosphate, Tribasic → 2-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-5-methyl-1,3,4-oxadiazole

HRID 634197
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HRID 634197 반응식
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:12][C:13]([CH3:16])=[N:14][N:15]=3)[CH:9]=2)[N:4]([S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:3]=1.[CH:27]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[N:32]=1)([CH3:29])[CH3:28].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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]>[CH:27]([O:30][C:31]1[N:32]=[C:33]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]4[O:12][C:13]([CH3:16])=[N:14][N:15]=4)[CH:9]=3)[N:4]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([CH3:24])=[CH:25][CH:26]=3)(=[O:18])=[O:19])[CH:3]=2)[CH:34]=[CH:35][CH:36]=1)([CH3:29])[CH3:28]
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참가 물질

6

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 426146482-Isopropoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 683282742-(3-Iodo-1-tosyl-1H-indol-5-yl)-5-methyl-1,3,4-oxadiazole

생성물 1

HCID 683285952-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-5-methyl-1,3,4-oxadiazole

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

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온도
120 °C

실험 절차

2-(3-Iodo-1-tosyl-1H-indol-5-yl)-5-methyl-1,3,4-oxadiazole (113 mg, 0.236 mmol), 2-isopropoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (74.4 mg, 0.283 mmol) (Combiphos Catalysts Inc.), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (6.74 mg, 0.014 mmol) (Strem), Pd2(dba)3 (6.48 mg, 7.07 μmol) (Strem), and potassium phosphate (150 mg, 0.707 mmol) (Reidel-de Haen) were weighed into a 20 mL glass microwave vial, which was then purged with argon. The solids were treated with dioxane (2.5 mL) and H2O (0.25 mL), the tube was sealed, and the contents were heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 120° C. for 15 min. The mixture was treated with 1N NaOH and extracted with EtOAc. The combined organic layers were dried, filtered and concentrated to give the crude product.

후처리

  1. customwas then purged with argon
  2. additionThe solids were treated with dioxane (2.5 mL) and H2O (0.25 mL)
  3. customthe tube was sealed
  4. additionThe mixture was treated with 1N NaOH
  5. extractionextracted with EtOAc
  6. customThe combined organic layers were dried
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-36ce5d484c2342fabeba90582eeea908
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321756B2

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