Cesium carbonate → HCID 66556099, compound

HRID 1629939Notes

Reaction equation

HRID 1629939 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)O1.Cl[C:20]1[CH:25]=[N:24][CH:23]=[C:22]([N:26]2[CH2:30][CH2:29][C:28]([F:32])([F:31])[CH2:27]2)[N:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C(Cl)(Cl)Cl>[F:32][C:28]1([F:31])[CH2:29][CH2:30][N:26]([C:22]2[N:21]=[C:20]([C:9]3[CH:10]=[C:11]4[CH:17]=[CH:16][NH:15][C:12]4=[N:13][CH:14]=3)[CH:25]=[N:24][CH:23]=2)[CH2:27]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 86681768HCID 86681768, compound

Product 1

HCID 66556099HCID 66556099, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A stirred solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (124) (50 mg, 1 eq) and 2-chloro-6-(3,3-difluoropyrrolidin-1-yl)pyrazine (54) (1 eq) in 1,4-dioxane (5 mL) was degassed and purged under argon atmosphere for 10 min. To this reaction mixture was charged Cs2CO3 (2 eq) followed by addition of Pd(dpp)Cl2 (0.04 eq) and degassing and purging under argon for additional 10 min. The reaction mixture was heated at 100° C. for 12 h in a sealed tube. After completion of the reaction, the reaction mixture was diluted with CHCl3 and filtered through Celite. The solvents were distilled off and the crude material was submitted for flash column purification in neutral alumina using 1% MeOH/CHCl3 to obtain pale yellow solid compound 5-(6-(3,3-difluoropyrrolidin-1-yl)pyrazin-2-yl)-1H-pyrrolo[2,3-b]pyridine 135 in 6 mg quantity.

Workup

  1. custompurged under argon atmosphere for 10 min
  2. customdegassing
  3. custompurging under argon for additional 10 min
  4. customAfter completion of the reaction
  5. filtrationfiltered through Celite
  6. distillationThe solvents were distilled off
  7. customthe crude material was submitted for flash column purification in neutral alumina using 1% MeOH/CHCl3

Sources & evidence

ORD record
ord-4da8915d7fb842e3849c83f044ef9678
Source dataset
uspto-grants-2014_07
Patent number
US08791112B2

Reaction notes

Loading…