Sodium Carbonate → HCID 86696690, compound

HRID 1774191Notes

Reaction equation

HRID 1774191 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][C:8]1[C:13]([F:14])=[C:12](B(O)O)[CH:11]=[CH:10][N:9]=1.[Cl:18][C:19]1[N:24]=[C:23](Cl)[CH:22]=[CH:21][N:20]=1.B(O)O>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O>[Cl:18][C:19]1[N:24]=[C:23]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]([Cl:7])[C:13]=2[F:14])[CH:22]=[CH:21][N:20]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 775312,4-DichloropyrimidineHCID 33023102-Chloro-3-fluoropyridine-4-boronic acid

Product 1

HCID 86696690HCID 86696690, compoundYield 72.1%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

Sodium carbonate (2.13 g, 20.1 mmol) was added to 2-chloro-3-fluoropyridin-4-ylboronic acid (1.41 g, 8.05 mmol) and 2,4-dichloropyrimidine (1.0 g, 6.71 mmol) in 4:1 dioxane/water (50 mL), and the mixture was sparged with argon. PdCl2(dppf)*DCM (0.274 g, 0.336 mmol) was added, and the mixture was heated at 80° C. under argon. After 4.5 hours, more boronic acid (approximately 0.2 g) was added and heating continued for a total of 8.5 hours. The reaction mixture was diluted with water, and the resulting solid was collected by vacuum filtration to afford the desired 2-chloro-4-(2-chloro-3-fluoropyridin-4-yl)pyrimidine (1.18 g, 4.84 mmol, 72.0% yield) with minor impurities.

Workup

  1. customthe mixture was sparged with argon
  2. temperatureheating
  3. customcontinued for a total of 8.5 hours
  4. filtrationthe resulting solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-b59a930b59f7439fb70282d3ed27aab0
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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