Pyrrole → HCID 57829605, compound

HRID 547486Notes

Reaction equation

HRID 547486 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.[NH:25]1[CH:29]=[CH:28][CH:27]=[CH:26]1.[C:30](=[O:33])([O-])[O-].[Cs+].[Cs+].[NH:36]1[CH2:43][CH2:42][CH2:41][C@H]1C(O)=O>CS(C)=O.[Cu]I>[N:36]1([C:30]([C:27]2[CH:28]=[CH:29][N:25]([C:2]3[N:3]=[C:4]4[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]4=[N:6][CH:7]=3)[CH:26]=2)=[O:33])[CH2:41][CH2:42][CH2:43]1

Participants

7

Reactant 4

HCID 8027PyrroleHCID 10796Cesium carbonateHCID 145742L-ProlineHCID 578292211-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-yl)-2,2-dimethylpropane-1-one

Product 1

HCID 57829605HCID 57829605, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.578 g, 0.432 mmol), pyrrole y (0.059 g, 0.39 mmol), cesium carbonate (0.256 g, 0.786 mmol), copper (I) iodide (0.008 g, 0.04 mmol) and proline (0.009 g, 0.08 mmol) in 0.8 mL of dimethylsulfoxide was stirred at 90° C. for 64 h then allowed to cool. The mixture was partitioned between 50 mL of ethyl acetate and 25 mL of water, and the aqueous layer was extracted with 50 mL of ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated to a residue. Column chromatography (0->3% MeOH/CH2Cl2) afforded 0.066 g (32%) of 1-[2-[3-(azetidine-1-carbonyl)-pyrrol-1-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow oil.

Workup

  1. temperatureto cool
  2. customThe mixture was partitioned between 50 mL of ethyl acetate and 25 mL of water
  3. extractionthe aqueous layer was extracted with 50 mL of ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-bcd992fe7b0b4368ba6451f70f758cb8
Source dataset
uspto-grants-2011_05
Patent number
US07939531B2

Reaction notes

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