Potassium Carbonate → HCID 59333308, compound

HRID 1893481Notes

Reaction equation

HRID 1893481 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])[C:8]3[N:9]2[CH:12]=[CH:13][N:14]=3)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[CH3:24][C:25]1(C)C(C)(C)OB(C=C)O1.C(B1OC(C)(C)C(C)(C)O1)=C.C(=O)([O-])[O-].[K+].[K+]>C(#N)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>[F:21][C:20]([F:23])([F:22])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[CH:24]=[CH2:25])[N:9]1[CH:12]=[CH:13][N:14]=[C:8]1[C:7]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])=[N:6]2

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 59333307HCID 59333307, compoundHCID 131730815HCID 131730815, compound2×

Product 1

HCID 59333308HCID 59333308, compoundYield 14%

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalyst2×HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst2×HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(8-bromo-7-trifluoromethyl-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol prepared as in example 52 (1 g; 2.57 mmol; 1 eq), 1,1′bis(diphenylphosphino) ferrocene)palladium dichloride. Dichloromethane complex (210 mg; 0.257 mmol; 0.1 eq), vinylboronic acid pinacol ester 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (700 μl; 4.1 mmol; 1.6 eq), potassium carbonate (1.42 g; 10.28 mmol; 4 eq) in acetonitrile (12 ml) and water (4 ml) is stirred 24 h at 65° C. under argon. The conversion being slow the reaction mixture is stirred for 3 additional days at 65° C. under argon with daily addition of 1,1′bis(diphenylphosphino) ferrocene)palladium dichloride. dichloromethane complex (105 mg; 0.129 mmol; 0.05 additional eq) and vinylboronic acid pinacol ester 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (500 μl; 2.9 mmol; 1.1 additional eq). Concentration, partition (ethyl acetate/water), extraction of the aqueous phase (ethyl acetate), reunion of the organic phases, drying (magnesium sulphate) and purification by flash chromatography on silica gel (gradient of methanol 0 to 20% in dichloromethane) followed by trituration in methanol afforded the title compound (118 mg; 0.351 mmol; 14%) as a pale yellow powder.

Workup

  1. concentrationConcentration
  2. custompartition
  3. extraction(ethyl acetate/water), extraction of the aqueous phase (ethyl acetate), reunion of the organic phases
  4. customdrying
  5. custom(magnesium sulphate) and purification by flash chromatography on silica gel (gradient of methanol 0 to 20% in dichloromethane)

Sources & evidence

ORD record
ord-b36642ee436a49798cfad0703f6f3488
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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