Potassium Carbonate → 3-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)-5-(1H-indol-5-yl)-2-pyridinamine

HRID 632478Notes

Reaction equation

HRID 632478 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[O:10][C:11]([CH:14]3[CH2:16][CH2:15]3)=[N:12][N:13]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[NH:17]1[C:25]2[C:20](=[CH:21][C:22](B(O)O)=[CH:23][CH:24]=2)[CH:19]=[CH:18]1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>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.O>[CH:14]1([C:11]2[O:10][C:9]([C:4]3[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:22]4[CH:21]=[C:20]5[C:25](=[CH:24][CH:23]=4)[NH:17][CH:18]=[CH:19]5)[CH:3]=3)=[N:13][N:12]=2)[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27343615-Indolylboronic acidHCID 902729865-Bromo-3-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-2-pyridinamine

Product 1

HCID 771069603-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)-5-(1H-indol-5-yl)-2-pyridinamine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-3-(5-cyclopropyl-[1,3,4]oxadiazol-2-yl)-pyridin-2-ylamine (200 mg, 0.71 mmol), 5-indolyl boronic acid (112 mg, 0.78 mmol), K2CO3 (290 mg, 2.13 mmol), 1,4-dioxane (10.0 mL) and water (4.0 mL) were taken in a sealed tube and degassed with nitrogen for 15 min. Then Pd(PPh3)4 (41 mg, 0.03 mmol) was added and stirred for 18 h at 100° C. The reaction mixture was diluted with ice-cold water and extracted with EtOAc. The combined extracts were dried over Na2SO4 and evaporated under reduced pressure to get crude 3-(5-cyclopropyl-[1,3,4]oxadiazol-2-yl)-5-(1H-indol-5-yl)-pyridin-2-ylamine. Crude compound was purified by column chromatography using silica gel (100-200 mesh). The column was eluted with 30% EtOAc in petroleum ether to afford the title compound as a pale yellow solid.

Workup

  1. customdegassed with nitrogen for 15 min
  2. additionThe reaction mixture was diluted with ice-cold water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. customevaporated under reduced pressure
  6. customto get crude 3-(5-cyclopropyl-[1,3,4]oxadiazol-2-yl)-5-(1H-indol-5-yl)-pyridin-2-ylamine
  7. customCrude compound was purified by column chromatography
  8. washThe column was eluted with 30% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-d3fbb130bef24cf4a786e797d028a6de
Source dataset
uspto-grants-2016_04
Patent number
US09321748B2

Reaction notes

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