Potassium Carbonate → HCID 59540613, compound

HRID 1677530Notes

Reaction equation

HRID 1677530 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1.[CH3:25][O:26][CH2:27][O:28][C:29]1[CH:30]=[C:31]([N:44]2[CH2:48][CH2:47][CH2:46][CH2:45]2)[CH:32]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:34]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>O>[CH3:25][O:26][CH2:27][O:28][C:29]1[CH:34]=[C:33]([C:2]2[N:3]=[C:4]3[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]3=[N:6][CH:7]=2)[CH:32]=[C:31]([N:44]2[CH2:48][CH2:47][CH2:46][CH2:45]2)[CH:30]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 578292211-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-yl)-2,2-dimethylpropane-1-oneHCID 59540635HCID 59540635, compound

Product 1

HCID 59540613HCID 59540613, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A microwave flask was charged with 1-[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (705 mg, 1.71 mmol, following the general procedures described in these Examples), 1-[3-methoxymethoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyrrolidine (570 mg, 1.71 mmol), and K2CO3 (591 mg, 4.28 mmol). Dioxane (13 ml) and water (3.2 ml) were added, and the solution was vacuum degassed under argon. [1,1′-Bis(diphenylphosphino)ferrocene]palladium(ll) dichloride dichloromethane complex (140 mg, 0.17 mmol) was added, and the reaction mixture was heated (150° C.) in a microwave reactor for 45 minutes. The reaction mixture was filtered through a plug of celite using ethyl acetate. The filtrate was transferred to a reparatory funnel and shaken with water (60 ml). The organic phase was collected and the aqueous phase back extracted with ethyl acetate (2×50 ml). The organic phases were combined, dried (MgSO4), filtered and stripped to provide a viscous semi-solid. This material was purified by preparative TLC, eluting with 24% ethyl acetate in hexanes to afford 492 mg of 1-[2-(3-Methoxymethoxy-5-pyrrolidin-1-yl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a red-brown viscous oil.

Workup

  1. customdegassed under argon
  2. addition[1,1′-Bis(diphenylphosphino)ferrocene]palladium(ll) dichloride dichloromethane complex (140 mg, 0.17 mmol) was added
  3. filtrationThe reaction mixture was filtered through a plug of celite
  4. customThe filtrate was transferred to a reparatory funnel
  5. customThe organic phase was collected
  6. extractionthe aqueous phase back extracted with ethyl acetate (2×50 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customto provide a viscous semi-solid
  10. customThis material was purified by preparative TLC
  11. washeluting with 24% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2278fc8ff31d4549aa5428d851a70ff8
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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