Potassium Carbonate → HCID 89690245, compound

HRID 517926Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture comprising 7-chloro-2,3-di-p-tolylpyrido[2,3-b]pyrazine (step 1) (2.5 g, 7.24 mmol), ethyl boronic acid (0.748 g, 10.14 mmol) and K2CO3 (2.9 g, 21.73 mmol) was degassed with argon and treated with Pd(PPh3)4(0.418 g, 0.362 mmol). The resulting mixture was flushed with argon and heated at 100° C. for 12 h and heating continued overnight. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated under vacuum. Purification of the crude product by chromatography on silica eluting with 10% EtOAc in hexane afforded the titled compound;

Workup

customThe resulting mixture was flushed with argon
temperatureheating
additionThe reaction mixture was diluted with water
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulphate
concentrationconcentrated under vacuum
customPurification of the crude product by chromatography on silica eluting with 10% EtOAc in hexane

Sources & evidence

ORD record: ord-c776e78639fe426497427938e228887b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115129B2

Reaction notes

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