Potassium Carbonate → 5-(1H-indol-5-yl)-3-(5-isopropyl-1,3,4-oxadiazol-2-yl)pyridin-2-amine

HRID 632477Notes

Reaction equation

HRID 632477 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[O:10][C:11]([CH:14]([CH3:16])[CH3:15])=[N:12][N:13]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[NH:23]1[C:31]2[C:26](=[CH:27][C:28](B(O)O)=[CH:29][CH:30]=2)[CH:25]=[CH:24]1>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:23]1[C:31]2[C:26](=[CH:27][C:28]([C:2]3[CH:3]=[C:4]([C:9]4[O:10][C:11]([CH:14]([CH3:16])[CH3:15])=[N:12][N:13]=4)[C:5]([NH2:8])=[N:6][CH:7]=3)=[CH:29][CH:30]=2)[CH:25]=[CH:24]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343615-Indolylboronic acidHCID 902732895-Bromo-3-(5-isopropyl-[1,3,4]oxadiazol-2-yl)-pyridin-2-ylamine

Product 1

HCID 771063645-(1H-indol-5-yl)-3-(5-isopropyl-1,3,4-oxadiazol-2-yl)pyridin-2-amine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-3-(5-isopropyl-[1,3,4]oxadiazol-2-yl)-pyridin-2-ylamine (250 mg, 0.883 mmol) in dioxane (15 mL) and water (7 mL) were added K2CO3 (365 mg, 2.649 mmol), indole-5-boronic acid (156 mg, 0.971 mmol) in a sealed tube. The reaction mixture was degassed by N2 for 20 min, then Pd(PPh3)4 (102 mg, 0.088 mmol) was added and stirred for 18 h at 100° C. Water (20 mL) was added and extracted with ethyl acetate (3×20 mL) and the organic layer was washed with brine, dried over anhydrous sodium sulphate, and concentrated under reduced pressure. Crude product was purified by column chromatography using 100-200 mesh silica gel compound eluted with 40% ethyl acetate in petroleum ether to afford the title compound as a yellow solid.

Workup

  1. customThe reaction mixture was degassed by N2 for 20 min
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customCrude product was purified by column chromatography
  7. washeluted with 40% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-2eff453f71cd430b83a503f7f8aaa832
Source dataset
uspto-grants-2016_04
Patent number
US09321748B2

Reaction notes

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