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

HRID 634197Notes

Reaction equation

HRID 634197 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-36ce5d484c2342fabeba90582eeea908
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

Loading…