Sodium Carbonate → 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-N-(2-methoxy-phenyl)-benzamide

HRID 1848601Notes

Reaction equation

HRID 1848601 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[Cl:7][C:8]1[CH:24]=[CH:23][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[O:13])=[CH:10][C:9]=1B1OC(C)(C)C(C)(C)O1.Br[C:35]1[C:40]([Cl:41])=[CH:39][C:38]([Cl:42])=[CH:37][N:36]=1>C1(C)C=CC=CC=1.CCO.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>[Cl:7][C:8]1[CH:24]=[CH:23][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[O:13])=[CH:10][C:9]=1[C:35]1[C:40]([Cl:41])=[CH:39][C:38]([Cl:42])=[CH:37][N:36]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 8170902-Bromo-3,5-dichloropyridineHCID 686032344-chloro-N-(2-methoxy-phenyl)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide

Product 1

HCID 686027194-chloro-3-(3,5-dichloro-pyridin-2-yl)-N-(2-methoxy-phenyl)-benzamideYield 67.1%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
100 °C

Procedure

A solution of 2N Na2CO3 (5.85 mL) and Pd(PPh3)4 (340 mg, 0.29 mmol) was added to a degassed mixture of 4-chloro-N-(2-methoxy-phenyl)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (2.2 g, 5.85 mmol) and 2-bromo-3,5-dichloro-pyridine (1.47 g, 6.44 mmol) in toluene (30 mL) and EtOH (6 mL). The mixture was heated at 100° C. for 12 hrs. Upon cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water and brine, and was dried over Na2SO4. After filtration and concentration the mixture was taken up in EtOAc, filtered, washed with EtOAc (3×), MeOH and ether to yield 1.6 g of 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-N-(2-methoxy-phenyl)-benzamide. MS [M+H]+: 406.9; tR=3.03 min. (method 1)

Workup

  1. temperatureUpon cooling to room temperature
  2. washwashed with water and brine
  3. dry with materialwas dried over Na2SO4
  4. filtrationAfter filtration and concentration the mixture
  5. filtrationfiltered
  6. washwashed with EtOAc (3×), MeOH and ether

Sources & evidence

ORD record
ord-958912824e1d44d5a3d4e14986f77894
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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