Sodium Carbonate → HCID 86680607, compound

HRID 1497431Notes

Reaction equation

HRID 1497431 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=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>[CH3:10][O:11][C:12]1[CH:17]=[C:16]([C:2]2[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 86680607HCID 86680607, compoundYield 65%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
77.5 °C

Procedure

To a solution of 5-bromopicolinaldehyde (1.0 g, 5.43 mmol) in toluene (10 mL) and ethanol (8 mL) was added (3-methoxyphenyl)boronic acid (1.2 g, 8.1 mmol), 2M sodium carbonate (3.4 g, 32.6 mmol, 8 mL water), Pd(PPh3)4 (0.228 g, 0.25 mmol) under argon. The resulting mixture was heated at 75-80° C., for 4 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, which was distilled off to obtain the crude product. The crude product was purified by flash chromatography (100-200 microns; 15% ethyl acetate in hexane) to afford 5-(3-methoxyphenyl)picolinaldehyde (0.75 g, 65% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.02 (s, 1H), 9.14 (s, 1H), 8.33 (d, 1H), 7.98 (d, 1H), 7.45 (t, 1H), 7.38 (d, 2H), 7.03 (d, 1H), 3.84 (s, 3H); LC-MS m/z calculated for [M+H]+ 214.08 found, 214.3.

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, which
  4. distillationwas distilled off
  5. customto obtain the crude product
  6. customThe crude product was purified by flash chromatography (100-200 microns; 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b4b169033c2844848fa3ee223a3ca4cb
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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