Sodium Carbonate → HCID 60209553, compound

HRID 2246209Notes

Reaction equation

HRID 2246209 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]([NH:20][CH3:21])=[O:19])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[F:22][C:23]([F:35])([F:34])[O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(C)C=CC=CC=1>[F:22][C:23]([F:34])([F:35])[O:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]([NH:20][CH3:21])=[O:19])=[O:15])[CH2:10][CH2:9]3)=[N:6][CH:7]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 60209559HCID 60209559, compound

Product 1

HCID 60209553HCID 60209553, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

The process is performed according to the procedure described in Example 2 (step 2.4.). Starting with 0.250 g (0.61 mmol) of 2-(methylamino)-2-oxoethyl 4-(5-iodo-2-pyridyl)-1-piperazinecarboxylate, obtained in step 5.5., 0.51 g (2.44 moles) of 4-(trifluoromethoxy)-phenylboronic acid, 0.61 g (˜8 mol %) of palladium catalyst on a solid support, prepared in step 2.1. of Example 2, and 2.9 ml (7.32 mmol) of aqueous sodium carbonate solution (2.5M) suspended in 12 ml of toluene and 3 ml of ethanol, and after chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol, followed by washing with diisopropyl ether, 0.092 g of product is obtained in the form of a white solid.

Workup

  1. customobtained in step 5.5
  2. wash3 ml of ethanol, and after chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol
  3. washby washing with diisopropyl ether

Sources & evidence

ORD record
ord-0faf4cdd5c954114b70f4c76185916ce
Source dataset
uspto-grants-2010_03
Patent number
US07687503B2

Reaction notes

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