Sodium Carbonate → HCID 86680620, compound

HRID 1497449Notes

Reaction equation

HRID 1497449 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[O:11]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12]1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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:11]1[CH:15]=[CH:14][C:13]([C:2]2[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=2)=[CH:12]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

Product 1

HCID 86680620HCID 86680620, compoundYield 74.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(5-bromopyridin-2-yl)ethanone (0.5 g, 2.5 mmol) in toluene (10 mL) and ethanol (5 mL) was added furan-3-ylboronic acid (0.335 g, 3.0 mmol) and a 2 M solution of aq. Na2CO3. The reaction mixture was degassed with argon, Pd(PPh3)4 (0.144 g, 0.125 mmol) was added, the reaction mixture was degassed with argon for 10 min, and the reaction was heated to 100° C. for 4 h. The reaction mixture was evaporated under vacuum to remove the ethanol, diluted with water (30 mL), extracted with ethyl acetate (100 mL), dried over sodium sulphate, filtered and evaporated under reduced pressure to obtain crude product. The crude product was purified by Biotage Isolera® One column (using 10% ethyl acetate and hexane) to give 1-(5-(furan-3-yl)pyridin-2-yl)ethanone (0.35 g, 74% yield); 1H NMR (400 MHz, DMSO-d6): δ 9.00 (s, 1H), 8.44 (s, 1H), 8.20-8.17 (m, 1H); 7.95 (d, 1H), 7.83 (s, 1H), 7.13 (s, 1H), 2.57 (s, 3H): LC-MS m/z calcd for [M+H]+ 187.06. found 188.0.

Workup

  1. additionwas added
  2. customthe reaction mixture was degassed with argon for 10 min
  3. customThe reaction mixture was evaporated under vacuum
  4. customto remove the ethanol
  5. additiondiluted with water (30 mL)
  6. extractionextracted with ethyl acetate (100 mL)
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto obtain crude product
  11. customThe crude product was purified by Biotage Isolera® One column (using 10% ethyl acetate and hexane)

Sources & evidence

ORD record
ord-149f29b8a907453bbe0b10a93579f90b
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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