Methanol → HCID 58010044, compound

HRID 2204603Notes

Reaction equation

HRID 2204603 reaction equation
Br[C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[CH3:21][OH:22].[C]=O.CN([CH:28]=[O:29])C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[S:11]([N:8]1[C:5]2=[N:6][CH:7]=[C:2]([C:21]([O:29][CH3:28])=[O:22])[N:3]=[C:4]2[CH:10]=[CH:9]1)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 529876432-Bromo-5-((4-methylphenyl)sulfonyl)-5H-pyrrolo(2,3-b)pyrazineHCID 178418416HCID 178418416, compound

Product 1

HCID 58010044HCID 58010044, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
65 °C

Procedure

To a solution of 2-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (5.00 g, 14.2 mmol) in DMF (64 mL) were added dichlorobis(triphenylphosphine)palladium (0.60 g, 0.86 mmol), TEA (5.9 mL, 43 mmol), and MeOH (17 mL, 420 mmol). The reaction flask was fitted with a balloon filled with carbon monoxide. The flask was evacuated and back-filled with carbon monoxide twice and the mixture was heated at about 65° C. for about 3 h. Additional dichlorobis(triphenylphosphine) palladium (0.60 g, 0.86 mmol) was added and the flask was re-evacuated and back-filled with carbon monoxide twice. The reaction mixture was heated at about 95° C. for about 16 h under an atmosphere of carbon monoxide. The mixture was cooled to room temperature and poured into ice water (350 mL). The resulting suspension was stirred for about 10 min and filtered. The filter cake was washed with water and the solid was lyophilized for about 48 h to give methyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carboxylate (5.0 g, 90% UV purity, 95%) as a light brown solid: LC/MS (Table 2, Method a) Rt=2.21 min; MS m/z: 332 (M+H)+.

Workup

  1. customThe reaction flask was fitted with a balloon
  2. customThe flask was evacuated
  3. additionback-filled with carbon monoxide twice
  4. customthe flask was re-evacuated
  5. additionback-filled with carbon monoxide twice
  6. temperatureThe reaction mixture was heated at about 95° C. for about 16 h under an atmosphere of carbon monoxide
  7. temperatureThe mixture was cooled to room temperature
  8. additionpoured into ice water (350 mL)
  9. filtrationfiltered
  10. washThe filter cake was washed with water
  11. waitthe solid was lyophilized for about 48 h

Sources & evidence

ORD record
ord-32fa99d90471435bb9569d3a7e0d88e9
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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