Dichloromethane → HCID 59204906, compound

HRID 2241918Notes

Reaction equation

HRID 2241918 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].ClCCl.Br[C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:36])[C:28]2[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=2[OH:35])=[CH:22][C:21]=1[F:37]>O1CCOCC1.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].O>[Cl:34][C:32]1[CH:31]=[CH:30][C:29]([OH:35])=[C:28]([CH:33]=1)[C:27]([NH:26][C:23]1[CH:24]=[CH:25][C:20]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[C:21]([F:37])[CH:22]=1)=[O:36]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 59204940HCID 59204940, compound

Product 1

HCID 59204906HCID 59204906, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

4-Pyridineboronic acid (0.185 mg, 1.51 mmol), potassium carbonate (0.240 g, 1.74 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (0.189 g, 0.232 mmol) and water (0.5 ml) were added to a solution of N-(4-bromo-3-fluorophenyl)-5-chloro-2-hydroxybenzamide (compound of Reference Example 185; 0.400 g, 1.16 mmol) in dioxane (5 ml), and the mixture was stirred at 80° C. for 2 hours. Water was added to the reaction mixture, and the precipitated solid was collected by filtration and washed with acetone and dichloromethane to give the title compound (0.286 g, 72%) as a light grey solid.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with acetone and dichloromethane

Sources & evidence

ORD record
ord-4cbc159dcd8d4054b5fe0b38b112e2b6
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

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