Potassium Carbonate → HCID 25070420, compound

HRID 1893442Notes

Reaction equation

HRID 1893442 reaction equation
Br[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]([F:23])([F:22])[F:21])=[CH:9][CH:8]=3.[C:24]([NH:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)(=[O:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl.CO>COCCOC.O.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>[OH:19][CH2:18][CH2:17][CH2:16][NH:15][C:14]1[C:5]2[N:6]([C:2]([C:32]3[CH:33]=[C:28]([NH:27][C:24](=[O:26])[CH3:25])[CH:29]=[CH:30][CH:31]=3)=[CH:3][N:4]=2)[C:7]2[C:12]([N:13]=1)=[CH:11][C:10]([C:20]([F:23])([F:22])[F:21])=[CH:9][CH:8]=2

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 157274(3-Acetamidophenyl)boronic acidHCID 21226129Dichloromethane methanolHCID 25070093HCID 25070093, compound

Product 1

HCID 25070420HCID 25070420, compoundYield 60.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of 3-(1-Bromo-7-trifluoromethyl-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol (375 mg; 0.96 mmol; 1 eq) in a mixture of 1,2-dimethoxyethane and water (3.4 mL/1.4 mL), 3-acetamidophenylboronic acid (242 mg, 1.35 mmol; 1.4 eq) is added under argon followed by potassium carbonate (266 mg; 1.93 mmol; 2 eq) and tetrakis(triphenylphosphine)palladium (89 mg; 0.08 mmol; 0.08 eq). The solution is allowed to stir for 17 hours at 90° C. until the reaction is complete on TLC. The crude mixture is cooled to room temperature, diluted with ethyl acetate (15 mL) and washed with water (10 mL). The resulting organic phase is dried over sodium sulfate, filtered and concentrated under vacuum to afford a grey powder. This solid is passed through two successive columns (eluent column 1: ethyl acetate 100%; eluent column 2: methylene chloride/methanol 9:1) to afford the title compound as an off-white powder (256 mg; 0.58 mmol; 60%).

Workup

  1. additionis added under argon
  2. washwashed with water (10 mL)
  3. dry with materialThe resulting organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto afford a grey powder

Sources & evidence

ORD record
ord-c80dc698d3cd4cfb96521245ba540afd
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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