Cesium carbonate → HCID 86603154, compound

HRID 736340Notes

Reaction equation

HRID 736340 reaction equation
[C:1]([O-])([O-])=O.[Cs+].[Cs+].[Br:7][C:8]1[CH:9]=[C:10]([C:14]([C:16]2[C:24]3[C:23]([Cl:25])=[N:22][CH:21]=[N:20][C:19]=3[NH:18][CH:17]=2)=[O:15])[CH:11]=[N:12][CH:13]=1>CN(C=O)C>[Br:7][C:8]1[CH:9]=[C:10]([C:14]([C:16]2[C:24]3[C:23]([Cl:25])=[N:22][CH:21]=[N:20][C:19]=3[N:18]([CH3:1])[CH:17]=2)=[O:15])[CH:11]=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 86603153HCID 86603153, compound

Product 1

HCID 86603154HCID 86603154, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cs2CO3 (2.32 g, 7.11 mmol) was added to a suspension of (5-Bromo-pyridin-3-yl)-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (1.0 g, 5.93 mmol) in DMF (60 mL) at room temperature. The resulting mixture was stirred for 30 min. Mel (1.01 g, 7.11 mmol) was added and the reaction and stirred for 2 h at room temperature. The reaction mixture was quenched with water (30 mL) and extracted with hot EtOAc (3×50 mL). The combined extracts were washed with brine (100 mL), dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash column chromatography (ethyl acetate/hexanes 2:8-7:3) provided a solid. The solid was triturated with EtOAc to provide the title compound as an off white solid (1.52 g, 73%). MS: 351.9/353.9 (MH+); HPLC Rf: 4.45 min. (HPLC method 4).

Workup

  1. additionMel (1.01 g, 7.11 mmol) was added
  2. customthe reaction
  3. stirringstirred for 2 h at room temperature
  4. customThe reaction mixture was quenched with water (30 mL)
  5. extractionextracted with hot EtOAc (3×50 mL)
  6. washThe combined extracts were washed with brine (100 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by flash column chromatography (ethyl acetate/hexanes 2:8-7:3)
  11. customprovided a solid
  12. customThe solid was triturated with EtOAc

Sources & evidence

ORD record
ord-b53dbec479a843d29204f13b05f6b969
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

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