Potassium Carbonate → HCID 44208751, compound

HRID 1677397Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.ClC1N=C2C(C(=O)CC(C)C)=CNC2=NC=1.C(=O)([O-])[O-].[K+].[K+].[CH3:39][O:40][C:41]1[CH:42]=[C:43](B(O)O)[CH:44]=[C:45]([O:49][CH3:50])[C:46]=1[O:47][CH3:48]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:14][CH:13]([CH3:15])[CH2:12][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:43]3[CH:44]=[C:45]([O:49][CH3:50])[C:46]([O:47][CH3:48])=[C:41]([O:40][CH3:39])[CH:42]=3)[N:3]=2)[NH:8][CH:9]=1)=[O:16]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-3-methyl-butan-1-one and 1-(2-chloro-5H-pyrrolo[2,3-b]pyrazin-7-yl)-3-methyl-butan-1-one (55 mg), potassium carbonate (95 mg, 0.69 mmol), 3,4,5-trimethoxyphenylboronic acid (47 mg, 0.22 mmol) and Pd(dppf)Cl2-DCM (16 mg, 0.02 mmol) was placed in a 5 ml microwave vial. The vial was capped and purged with nitrogen. Solvent was added (2 ml of 20% aqueous dioxane) and the vial was purged again with nitrogen. The reaction mixture was heated in a microwave reactor at 150° C. for 30 min. The solvents were evaporated and the crude product was purified by flash chromatography using a gradient of 20% ethyl acetate in hexanes up to 50% to yield 30 mg of 3-methyl-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butan-1-one. MS: (M+H)+=370, MP=210.0-211.4° C.

Workup

customThe vial was capped
custompurged with nitrogen
additionSolvent was added (2 ml of 20% aqueous dioxane)
customthe vial was purged again with nitrogen
customThe solvents were evaporated
customthe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-1c93900414dc4600a437dad9b6ec02d0
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008298B2

Reaction notes

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