Sodium Carbonate → HCID 86680613, compound

HRID 1497439Notes

Reaction equation

HRID 1497439 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[C:10]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)(=[O:12])[NH2:11].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>[CH:8]([C:5]1[N:6]=[CH:7][C:2]([C:16]2[CH:17]=[CH:18][C:13]([C:10]([NH2:11])=[O:12])=[CH:14][CH:15]=2)=[CH:3][CH:4]=1)=[O:9]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27378114-Aminocarbonylphenylboronic acidHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 86680613HCID 86680613, compoundYield 62.3%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
77.5 °C

Procedure

To a solution of 5-bromo picolinaldehyde (0.7 g, 3.76 mmol) in toluene (100 mL) and ethanol (75 mL) was added (4-carbamoylphenyl)boronic acid (1.24 g, 7.52 mmol), 2M sodium carbonate (2.8 g, 26.32 mmol, 6 mL water), Pd(PPh3)4 (0.217 g, 0.188 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 crude product was purified by flash chromatography (100-200μ; 35% ethyl acetate in hexane) to afford 4-(6-formylpyridin-3-yl)benzamide (0.53 g, 62% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.03 (s, 1H), 9.20 (s, 1H), 8.39 (d, 1H), 8.07 (s, 1H), 8.03 (d, 3H), 7.93 (d, 2H), 7.44 (s, 1H).

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 crude product was purified by flash chromatography (100-200μ; 35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-dc6c7e3db4ea4cecbbd5b75a750531c0
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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