Potassium Carbonate → 2,2-Dimethyl-1-[2-(6-morpholin-4-yl-pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one

HRID 547473Notes

Reaction equation

HRID 547473 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[CH:27][C:28]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[N:29][CH:30]=2)O1.C([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][C:12]([CH3:15])([CH3:14])[C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:25]3[CH:30]=[N:29][C:28]([N:31]4[CH2:32][CH2:33][O:34][CH2:35][CH2:36]4)=[CH:27][CH:26]=3)[N:3]=2)[NH:8][CH:9]=1)=[O:16]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 441930962,2-Dimethyl-1-[2-(6-morpholin-4-yl-pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-oneYield 56.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (0.1 g, 0.354 mmol), commercially available 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]morpholine (0.206 g, 0.709 mmol), K2CO3 (0.147 g, 1.063 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.041 g, 35 micomol) in 3 mL of MeOH and 1 mL of DCM was degassed by bubbling argon through the mixture. It was then stirred at 110° C. for 25 minutes under microwave irradiation before being cooled to RT. And evaporated. The residue was adsorbed onto SiO2 and purified twice by SiO2 chromatography (hexanes/EtOAc 0-50% EtOAc, followed by DCM/MeOH 0-4% MeOH) to give 0.073 g of 2,2-Dimethyl-1-[2-(6-morpholin-4-yl-pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one (56% yield).

Workup

  1. customwas degassed
  2. customby bubbling argon through the mixture
  3. temperaturebefore being cooled to RT
  4. customAnd evaporated
  5. custompurified twice by SiO2 chromatography (hexanes/EtOAc 0-50% EtOAc, followed by DCM/MeOH 0-4% MeOH)

Sources & evidence

ORD record
ord-2dfcce6d1e31484fa70d896d92d431d3
Source dataset
uspto-grants-2011_05
Patent number
US07939531B2

Reaction notes

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