Potassium Carbonate → HCID 68502168, compound

HRID 734956Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[NH2:18][C:19]1[C:24]([S:25]([N:28]([CH3:30])[CH3:29])(=[O:27])=[O:26])=[CH:23][C:22](B2OC(C)(C)C(C)(C)O2)=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[NH2:18][C:19]1[C:24]([S:25]([N:28]([CH3:30])[CH3:29])(=[O:27])=[O:26])=[CH:23][C:22]([C:2]2[CH:11]=[C:10]3[C:5](=[CH:4][CH:3]=2)[N:6]=[CH:7][C:8]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:9]3)=[CH:21][N:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7-bromo-2-(4-pyridinyl)quinoxaline (0.245 mmol), 2-amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinesulfonamide (0.245 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.0196 mmol), 2M aqueous potassium carbonate (2 mL) and anhydrous 1,4-dioxane (6 mL) was heated at 100° C. for 4 h in a sealed pressure vessel. After cooling to room temperature, the organic layer was separated and purified directly on silica gel, eluting with 0-10% methanol in ethyl acetate followed by a second purification by HPLC (eluting with acetonitrile: 0.1% TFA in H2O) to afford the title compound as a bright yellow solid (47 mg, 47% yield). MS(ES)+ m/e 407.2 [M+H]+.

Workup

temperatureAfter cooling to room temperature
customthe organic layer was separated
custompurified directly on silica gel
washeluting with 0-10% methanol in ethyl acetate
customfollowed by a second purification by HPLC (eluting with acetonitrile: 0.1% TFA in H2O)

Sources & evidence

ORD record: ord-f033c6b22e864ed184143e9547cc2f8a
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592342B2

Reaction notes

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