Sodium Carbonate → HCID 82078553, compound

HRID 1497447Notes

Reaction equation

HRID 1497447 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=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>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=2)=[CH:14][CH:13]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

Product 1

HCID 82078553HCID 82078553, compoundYield 69.8%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
77.5 °C

Procedure

To a solution of 1-(5-bromopyridin-2-yl)ethanone (1.0 g, 4.99 mmol) in toluene (100 mL) and ethanol (50 mL) was added 4-fluoro phenyl-boronic acid (1.4 g, 9.99 mmol), 2M sodium carbonate (3.7 g, 34.99 mmol, 12 mL water), Pd(PPh3)4 (0.228 g, 0.25 mmol) under argon. The resulting mixture was heated at 75-80° C. for 6 h. The contents were cooled to room temperature, diluted with ethyl acetate (150 mL), and washed with bicarbonate solution (2×100 mL) and brine solution (2×100 mL). The organic layer was dried over sodium sulphate and distilled off to obtain the crude product. The product was purified by flash chromatography (100-200μ; 35% ethyl acetate in hexane) to afford 1-(5-(4-fluorophenyl)pyridin-2-yl)ethanone (0.75 g, 66% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.12 (s, 1H), 8.25 (dd, 1H), 8.00 (d, 1H), 7.86 (m, 2H), 7.36 (t, 2H), 2.65 (s, 3H); LC-MS m/z calculated for [M+H]+ 216.23 found, 216.0.

Workup

  1. temperatureThe contents were cooled to room temperature
  2. washwashed with bicarbonate solution (2×100 mL) and brine solution (2×100 mL)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. distillationdistilled off
  5. customto obtain the crude product
  6. customThe product was purified by flash chromatography (100-200μ; 35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ba6d3f30307b4c6d844fe319f47ea7a3
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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