Sodium Carbonate → HCID 25120170, compound

HRID 1893485Notes

Reaction equation

HRID 1893485 reaction equation
I[C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])[C:5]2=[N:4][CH:3]=1)=[CH:11][C:10]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]([F:29])([F:28])[F:27])=[CH:9][CH:8]=3.[NH:30]1[C:34](B(O)O)=[CH:33][CH:32]=[N:31]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[NH:30]1[C:34]([C:2]2[N:6]3[C:7]4[C:12]([N:13]=[C:14]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])[C:5]3=[N:4][CH:3]=2)=[CH:11][C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:27])[F:28])=[CH:9][CH:8]=4)=[CH:33][CH:32]=[N:31]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 112519791H-Pyrazole-5-boronic acidHCID 59333310HCID 59333310, compound

Product 1

HCID 25120170HCID 25120170, compoundYield 40.2%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-({1-iodo-7-[2-(trifluoromethyl)phenyl]imidazo[1,2-a]quinoxalin-4-yl}amino)propan-1-ol (42 mg; 0.082 mmol; 1 eq), 1,1′bis(diphenylphosphino) ferrocene)palladium dichloride. dichloromethane complex (20.1 mg; 0.025 mmol; 0.3 eq), 1H-pyrazole-5-boronic acid (18.3 mg; 0.164 mmol; 2 eq) and sodium carbonate (26 mg; 0.246 mmol; 3 eq) in anhydrous dimethylformamide (0.37 ml) is stirred under argon at 100° C. for 4 h. Partition (aqueous sodium hydrogenocarbonate/ethyl acetate), filtration over Celite, extraction of the aqueous phase (ethyl acetate), reunion of the organic phases, drying (magnesium sulphate) and purification by prep CCM on silicagel (dichloromethane/methanol 95:5) affords the title product (15 mg; 0.033 mmol; 39%) as an off-white solid.

Workup

  1. customPartition
  2. filtration(aqueous sodium hydrogenocarbonate/ethyl acetate), filtration
  3. extractionover Celite, extraction of the aqueous phase (ethyl acetate), reunion of the organic phases
  4. customdrying
  5. custom(magnesium sulphate) and purification by prep CCM on silicagel (dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-5d2a102d4e7c41f689e85e169d999d95
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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