Sodium Carbonate → 4-(5-Fluoropyrimidin-2-yl)benzaldehyde

HRID 2416500Notes

Reaction equation

HRID 2416500 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH:7]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:8].Cl[C:19]1[N:24]=[CH:23][C:22]([F:25])=[CH:21][N:20]=1>C(O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:25][C:22]1[CH:21]=[N:20][C:19]([C:12]2[CH:13]=[CH:14][C:9]([CH:7]=[O:8])=[CH:10][CH:11]=2)=[N:24][CH:23]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5834662-Chloro-5-fluoropyrimidineHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 226312524-(5-Fluoropyrimidin-2-yl)benzaldehydeYield 52%

Reagents, catalysts & solvents 4

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)CatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2M aq. Na2CO3 (7 mL) and 4-formylphenylboronic acid (1.35 g, 9.0 mmol) in ethanol (4 mL) was added to a solution of 2-chloro-5-fluoropyrimidine (922 mg, 7.0 mmol, prepared as described in Org. Prep. Proc. Int. 1995, 27, 600), and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.209 g, 0.35 mmol) in toluene (15 mL). The reaction mixture was heated to reflux for 6 h, cooled to room temperature, diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried with Na2SO4, and concentrated in vacuo. Purification by medium pressure liquid chromatography (SiO2, 20:1 hexanes/ethyl acetate) gave 732 mg (52%) of the title compound. MS 203 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. washwashed with sat. aq. NaHCO3 and brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by medium pressure liquid chromatography (SiO2, 20:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-657a15cbee0e40509cea9a8d74860a55
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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