Potassium Carbonate → HCID 90403061, compound

HRID 1049359Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].O1[CH2:29][CH2:28]OCC1>O>[CH3:10][NH:11][C:12]1[N:15]=[CH:29][C:28]([C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:10]=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=3)[CH:5]=[CH:4][N:3]=2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of Example A1 (0.380 g, 1.510 mmol) and 6-(methylamino)-3-pyridinylboronic (0.252 g, 1.661 mmol) in dioxane (8 mL) was sparged with Ar, treated with a solution of K2CO3 (0.417 g, 3.02 mmol) in water (2 mL) and heated at 90° C. for 16 h. The mixture was cooled to RT, treated with water and extracted with EtOAc (2×). The combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford N-methyl-4-((6-nitropyridin-3-yl)oxy)-[2,3′-bipyridin]-6′-amine (300 mg, 61%) as an orange amorphous solid. 1H NMR (400 MHz, DMSO-d6): δ 8.73 (d, J=2.5 Hz, 1H), 8.58 (d, J=2.8 Hz, 1H), 8.55 (d, J=5.6 Hz, 1H), 8.39 (d, J=8.9 Hz, 1H), 8.06 (dd, J=8.8, 2.5 Hz, 1H), 7.96 (dd, J=8.9, 2.9 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.00 (dd, J=5.6, 2.3 Hz, 1H), 6.87 (q, J=5.2 Hz, 1H), 6.48 (d, J=8.8 Hz, 1H), 2.80 (d, J=4.7 Hz, 3H); MS (ESI) m/z: 324.1 (M+H+).

Workup

temperatureThe mixture was cooled to RT
extractionextracted with EtOAc (2×)
washThe combined organics were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated to dryness
custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record: ord-b7a3edd91a6a4cc5ad0768857b508088
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382228B2

Reaction notes

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