Potassium Carbonate → HCID 90273378, compound

HRID 1053107Notes

Reaction equation

HRID 1053107 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:15][C:16]([C:19]3[C:20]([NH2:26])=[N:21][CH:22]=[C:23](Br)[CH:24]=3)=[N:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH3:33][N:34]1[C:42]2[C:37](=[CH:38][C:39](B(O)O)=[CH:40][CH:41]=2)[CH:36]=[CH:35]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>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:15][C:16]([C:19]3[C:20]([NH2:26])=[N:21][CH:22]=[C:23]([C:39]4[CH:38]=[C:37]5[C:42](=[CH:41][CH:40]=4)[N:34]([CH3:33])[CH:35]=[CH:36]5)[CH:24]=3)=[N:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27598671-Methyl-1H-indole-5-boronic acidHCID 90273397HCID 90273397, compound

Product 1

HCID 90273378HCID 90273378, compoundYield 73.2%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

To a solution of 4-[5-(2-amino-5-bromo-pyridin-3-yl)-[1,3,4]oxadiazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.1 g, 2.59 mmol) in dioxane (20 mL) and water (10 mL) were added K2CO3 (1.07 g, 7.77 mmol) and N-methylindole-5-boronic acid (0.50 g, 2.85 mmol) in a sealed tube. The reaction mixture was degassed with argon for 20 min, then Pd(PPh3)4 (0.15 g, 0.13 mmol) was added to the reaction mixture. The reaction mixture was stirred for 18 h at 100° C. The reaction was diluted with water (100 mL), extracted with ethyl acetate (2×150 mL) and organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to get crude compound. Crude compound was purified by column chromatography using 100-200 mesh silica gel compound eluted with 60% ethyl acetate in petroleum ether to afford 900 mg of the title compound which is further purified by washing with 20% chloroform in hexane to afford the title compound as a pale yellow solid.

Workup

  1. customThe reaction mixture was degassed with argon for 20 min
  2. extractionextracted with ethyl acetate (2×150 mL) and organic layer
  3. washwas washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto get crude compound
  7. customCrude compound was purified by column chromatography
  8. washeluted with 60% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-857e91c944c249a7a5d64dec31da94a0
Source dataset
uspto-grants-2016_07
Patent number
US09393248B1

Reaction notes

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