Potassium Carbonate → (1-methyl-cyclohexyl)-[2-(3-pyrrolidin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

HRID 1677378Notes

Reaction equation

HRID 1677378 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]([C:13]3([CH3:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[N:20]1([C:25]2[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>O>[CH3:19][C:13]1([C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:27]4[CH:28]=[CH:29][CH:30]=[C:25]([N:20]5[CH2:21][CH2:22][CH2:23][CH2:24]5)[CH:26]=4)[N:3]=3)[NH:8][CH:9]=2)=[O:12])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 41926693-(Pyrrolidino)phenylboronic acidHCID 44199730(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-(1-methyl-cyclohexyl)-methanone

Product 1

HCID 59540689(1-methyl-cyclohexyl)-[2-(3-pyrrolidin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanoneYield 62.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A microwave tube was charged with (2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-(1-methyl-cyclohexyl)-methanone (95 mg, 0.29 mmol), 3-pyrrolidino phenylboronic acid (62 mg, 0.32 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(ll) (19 mg, 0.02 mmol), and freshly grounded K2CO3 (102 mg, 0.74 mmol). Dioxane (3 ml) and water (0.7 ml) were added, and the reaction mixture was microwaved at 150° C. for 30 minutes. The reaction mixture was partitioned between EtOAc/water. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a dark brown solid. The residue was purified by silica gel chromatography using 10-50% EtOAc in hexanes as eluant to provide 70 mg (61%) of (1-methyl-cyclohexyl)-[2-(3-pyrrolidin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone as a yellow solid. MP 243-245.4° C., M+H=389.

Workup

  1. customthe reaction mixture was microwaved at 150° C. for 30 minutes
  2. customThe reaction mixture was partitioned between EtOAc/water
  3. customThe organic layers were collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customgiving a dark brown solid
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-aacbfb2ad35347fc81f63b088c2b4fcb
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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