Nitrogen → HCID 178526836, compound

HRID 2375900Notes

Reaction equation

N#N.I[C:4]1[C:5]([OH:13])=[N:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1.[S:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.C([O-])(=O)C.[K+]>CN(C=O)C.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>[N+:10]([C:8]1[CH:9]=[C:4]([C:18]2[S:14][CH:15]=[N:16][CH:17]=2)[C:5]([OH:13])=[N:6][CH:7]=1)([O-:12])=[O:11]

Participants

Conditions

Temperature: 120 °C

Procedure

N2 was bubbled through a solution of 3-iodo-5-nitropyridin-2-ol (1.33 g, 5.00 mmol), thiazole (2.13 g, 25.0 mmol), potassium acetate (1.47 g, 15.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.4 mmol) in DMF (10 mL) for 10 min. The mixture was then heated to 120° C. and stirred for 17 h. The solvents were removed in vacuo. The residue was stirred with methanol (5 mL) and dichloromethane (10 mL) for 30 min. The solids were collected by filtration, washed with dichloromethane (2 mL) and water (3×8 mL), and dried in vacuo to afford the title compound as an off-white solid. 1H-NMR (DMSO-d6, 400 MHz): δ=8.74 (d, J=2.8 Hz, 1H), 8.77 (s, 1H), 8.79 (d, J=2.8 Hz, 1H), 9.12 (s, 1H), 13.26 (s, br, 1H). MS (ES+): m/z 224.09 [MH+]. HPLC: tR=2.16 min (ZQ2000, polar—5 min).

Workup

customThe solvents were removed in vacuo
stirringThe residue was stirred with methanol (5 mL) and dichloromethane (10 mL) for 30 min
filtrationThe solids were collected by filtration
washwashed with dichloromethane (2 mL) and water (3×8 mL)
customdried in vacuo

Sources & evidence

ORD record: ord-6ae22910b9e84264bb6a38973b4fdb86
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465726B2

Reaction notes

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