Cesium carbonate → HCID 117652485, compound

HRID 1500820Notes

Reaction equation

HRID 1500820 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[C:10](I)=[CH:9][N:8]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:5]2=[N:6][CH:7]=1.[CH3:31][C:32]1[CH:40]=[C:39]2[C:35]([CH:36]=[C:37](B3OC(C)(C)C(C)(C)O3)[NH:38]2)=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(Cl)Cl>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:37]3[NH:38][C:39]4[C:35]([CH:36]=3)=[CH:34][CH:33]=[C:32]([CH3:31])[CH:40]=4)=[CH:9][N:8]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 532167846-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleHCID 117652562HCID 117652562, compound

Product 1

HCID 117652485HCID 117652485, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of 2-bromo-7-iodo-5-trityl-5H-pyrrolo[2,3-b]pyrazine (6) (100 mg, 0.1766 mmol), 6-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (7) (47 mg, 0.1766 mmol) in acetonitrile (5 mL) was added cesium carbonate (115.74 mg, 0.3532 mmol). The resulting reaction mixture was degassed, purged with nitrogen for 10 min followed by the addition of Pd(PPh3) Cl2.DCM (7.06 mg, 0.0088 mmol) to the reaction mixture, which was again degassed, purged with nitrogen for another 15 min. The final reaction mixture was stirred for 2 h at 90° C. in a seal tube. After completion of the reaction, the contents were allowed to cool to RT and was diluted with DCM (25 mL) and filtered through Celite bed. The organic layer was concentrated to get the crude. The resulting oil was purified by flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 27% ethyl acetate in hexane to afford pale yellow solid (30 mg) of compound 2-bromo-7-(6-methyl-1H-indol-2-yl)-5-trityl-5H-pyrrolo[2,3-b]pyrazine (8).

Workup

  1. customThe resulting reaction mixture
  2. customwas degassed
  3. custompurged with nitrogen for 10 min
  4. additionfollowed by the addition of Pd(PPh3) Cl2
  5. custompurged with nitrogen for another 15 min
  6. customThe final reaction mixture
  7. customAfter completion of the reaction
  8. temperatureto cool to RT
  9. filtrationfiltered through Celite bed
  10. concentrationThe organic layer was concentrated
  11. customto get the crude
  12. customThe resulting oil was purified by flash chromatography
  13. washThe compound was eluted at 27% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7f77eec0f8384386972218131f03ae38
Source dataset
uspto-grants-2015_12
Patent number
US09206188B2

Reaction notes

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