Sodium Carbonate → HCID 11195507, compound

HRID 1497458Notes

Reaction equation

HRID 1497458 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=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>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

Product 1

HCID 11195507HCID 11195507, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-(5-bromopyridin-2-yl)ethanone (1.0 g, 5.0 mmol) in toluene (30 mL) and ethanol (20 mL) was added (4-methoxyphenyl)boronic acid (1.52 g, 10 mmol), 2M Na2CO3 (14 mL), Pd(PPh3)4 (0.057 g, 0.05 mmol), the reaction was purged with argon and heated at 80° C. for about 6 h. The reaction mixture was concentrated, diluted with water (100 mL), and extracted with ethyl acetate (2×300 mL). The combined organic extracts were washed with brine solution (20 mL), organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by flash chromatography (silica gel, 60-120μ) using 10% ethyl acetate in hexane eluent to afford 1-(5-(4-methoxyphenyl)-pyridin-2-yl)ethanone as off white solid (1 g, 88% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.99 (s, 1H), 8.20 (d, 1H), 7.96 (d, 1H), 7.76 (d, 2H), 7.027 (d, 2H), 3.80 (s, 3H), 2.63 (s, 3H). LC-MS m/z calcd for [M+H]+ 228.09. found 228.2.

Workup

  1. customthe reaction was purged with argon
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water (100 mL)
  4. extractionextracted with ethyl acetate (2×300 mL)
  5. washThe combined organic extracts were washed with brine solution (20 mL), organic layer
  6. dry with materialwas dried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customto obtain crude product
  9. customThe crude product was purified by flash chromatography (silica gel, 60-120μ)

Sources & evidence

ORD record
ord-a8c949d36b4c4256ae73e292eb31e6e0
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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