Sodium Carbonate → HCID 178422913, compound

HRID 1893461Notes

Reaction equation

HRID 1893461 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[Si](C)(C)CCOC[N:30]1[C:34](B(O)O)=[CH:33][CH:32]=[N:31]1.[C:40](=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>CN(C)C=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>[CH3:40][C:34]1[CH:33]=[C:32]([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]([F:23])([F:22])[F:21])=[CH:9][CH:8]=4)[NH:31][N:30]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 21874652(1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)boronic acidHCID 25070093HCID 25070093, compound

Product 1

HCID 178422913HCID 178422913, compoundYield 36.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 3-(1-bromo-7-trifluoromethyl-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol (27 mg, 0.07 mmol), 1-[2-(trimethylsilyl)ethoxymethyl]-pyrazole-5-boronic acid (36 mg, 0.14 mmol) and sodium carbonate (22 mg, 0.21 mmol) in N,N-dimethylformamide (300 μL) degassed under argon for 10 minutes was added tetrakis(triphenylphosphine)palladium (24 mg, 0.021 mmol). The mixture was allowed to stir for 3 hours at 100° C. The crude mixture is cooled to room temperature, diluted with ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The organic phase was separated and the aqueous phase was extracted again twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 20/1) to afford the title compound (10 mg, 28%) as a colorless gum.

Workup

  1. customdegassed under argon for 10 minutes
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted again twice with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 20/1)

Sources & evidence

ORD record
ord-092fdd949d364401b1a67f906c848fce
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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