Potassium Carbonate → 3-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)-5-(3-(morpholinomethyl)phenyl)pyridin-2-amine

HRID 1053146Notes

Reaction equation

HRID 1053146 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.C([O-])([O-])=O.[K+].[K+].[O:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=2)[CH2:25][CH2:24]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>[CH:14]1([C:11]2[O:10][C:9]([C:4]3[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:32]4[CH:33]=[CH:34][CH:35]=[C:30]([CH2:29][N:26]5[CH2:27][CH2:28][O:23][CH2:24][CH2:25]5)[CH:31]=4)[CH:3]=3)=[N:13][N:12]=2)[CH2:16][CH2:15]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 110314093-(Morpholinomethyl)phenylboronic acidHCID 902729865-Bromo-3-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-2-pyridinamine

Product 1

HCID 771065643-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)-5-(3-(morpholinomethyl)phenyl)pyridin-2-amineYield 16.8%

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-cyclopropyl-[1,3,4]oxadiazol-2-yl)-pyridin-2-ylamine (400 mg; 1.42 mmol) in dioxane (10 mL) and water (6 mL) were added K2CO3 (587 mg; 4.26 mmol), (3-(morpholinomethyl)phenyl)boronic acid (348 mg; 1.56 mmol) in a sealed tube. The reaction mixture was degassed with argon for 30 min, then added Pd(PPh3)4 (82.0 mg; 0.07 mmol) to the reaction mixture. The reaction mixture was stirred for 18 h at 100° C. The reaction mixture was diluted with water (50 mL) extracted with ethyl acetate (2×50 mL) and organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Crude compound was purified by column chromatography using 100-200 mesh silica gel and eluted with 100% ethyl acetate, which is further purified by washing with 30% chloroform in hexane to afford 90 mg (Yield: 16.7%) of the title compound, as a yellow colour solid.

Workup

  1. customThe reaction mixture was degassed with argon for 30 min
  2. extractionextracted with ethyl acetate (2×50 mL) and organic layer
  3. washwas washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customCrude compound was purified by column chromatography
  7. washeluted with 100% ethyl acetate, which
  8. customis further purified
  9. washby washing with 30% chloroform in hexane

Sources & evidence

ORD record
ord-985fada449f149e3a360f255ac16bc69
Source dataset
uspto-grants-2016_07
Patent number
US09393248B1

Reaction notes

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