Cesium carbonate → HCID 72202514, compound

HRID 1754561Notes

Reaction equation

HRID 1754561 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[NH:18][N:17]=[CH:16][C:7]=3[C:8](=[O:15])[N:9]([CH:12]([CH3:14])[CH3:13])[C:10]=2[CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)O1>CN(C=O)C.CCOC(C)=O.C1COCC1.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]>[CH3:13][CH:12]([N:9]1[C:10]2[CH:11]=[C:2]([C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[CH:3]=[CH:4][C:5]=2[C:6]2[NH:18][N:17]=[CH:16][C:7]=2[C:8]1=[O:15])[CH3:14]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86679805HCID 86679805, compound

Product 1

HCID 72202514HCID 72202514, compoundYield 19%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 7-bromo-5-(propan-2-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (0.25 g, 0.82 mmol) in 8 mL of DMF placed in a microwave reactor are added caesium carbonate (0.8 g 2.5 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.25 g 1.22 mmol) and the catalyst PdCl2(dppf) (60 mg, 0.08 mmol). The reactor is sealed and the mixture is stirred for 20 minutes at 150° C. under microwave irradiation. The reaction medium is diluted with an EtOAc/THF mixture (50/50) and washed with water and then with saturated aqueous NaCl solution. The organic phase is dried over Na2SO4 and concentrated to dryness. After purification by flash chromatography (DCM/MeOH: 100/0 to 90/10), 45 mg of a white solid are obtained (yield: 19%).

Workup

  1. customThe reactor is sealed
  2. washwashed with water
  3. dry with materialThe organic phase is dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customAfter purification by flash chromatography (DCM/MeOH: 100/0 to 90/10), 45 mg of a white solid
  6. customare obtained (yield: 19%)

Sources & evidence

ORD record
ord-35c4dc6f07cb4255ba3ed601c867e07a
Source dataset
uspto-grants-2015_10
Patent number
US09169246B2

Reaction notes

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