Sodium Carbonate → HCID 86680623, compound

HRID 1497453Notes

Reaction equation

HRID 1497453 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[N+:11]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)([O-:13])=[O:12].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>[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=2)=[CH:16][CH:15]=1)([O-:13])=[O:12]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27735524-Nitrophenylboronic acidHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

Product 1

HCID 86680623HCID 86680623, 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 (100 mg, 0.5 mmol) in toluene (4 mL) and ethanol (2 mL) was added (4-nitrophenyl)boronic acid (160 mg, 1 mmol), 2M Na2CO3 (1.4 mL), and Pd(PPh3)4 (6 mg, 0.005 mmol), the reaction was purged with argon, and then heated at 80° C. for about 6 h. The reaction mixture was concentrated, diluted with water (50 mL), and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (10 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-nitrophenyl)pyridin-2-yl)ethanone as off white solid (105 mg, 86% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.14 (s, 1H), 8.40-8.34 (m, 3H), 8.08 (dd, 3H), 2.67 (s, 3H), LC-MS m/z calcd for [M+H]+ 243.07. found 243.2.

Workup

  1. customthe reaction was purged with argon
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water (50 mL)
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. washThe combined organic extracts were washed with brine solution (10 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-569370d533d64962a88721aee622a7cb
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

Loading…