Sodium Chloride → HCID 90403992, compound

HRID 1468974Notes

Reaction equation

[NH2:1][C:2]1[C:7]([F:8])=[C:6]([Sn](C)(C)C)[N:5]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[C:3]=1[Cl:17].Br[C:19]1[C:27]([F:28])=[CH:26][C:22]2=[N:23][O:24][N:25]=[C:21]2[CH:20]=1.C(OCC)(=O)C.[Na+].[Cl-]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:19]2[C:27]([F:28])=[CH:26][C:22]3=[N:23][O:24][N:25]=[C:21]3[CH:20]=2)[N:5]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[C:3]=1[Cl:17]

Participants

Conditions

Temperature: 70 °C

Procedure

Methyl 4-amino-3-chloro-5-fluoro-6-(trimethylstannyl)picolinate (320 mg, 0.86 mmol) and 5-bromo-6-fluorobenzo[c][1,2,5]oxadiazole (170 mg, 0.78 mmol) were combined in 5 mL dry N,N-dimethylformamide, deaerated with a stream of nitrogen for 15 min. Bis(triphenylphosphine)palladium(II) chloride (55 mg, 0.078 mmol) and cuprous iodide (15 mg, 0.078 mmol) were added and the mixture was heated to 70° C. for 4 h. The mixture was shaken with 20 mL ethyl acetate, 10 mL saturated NaCl, dried (Na2SO4) and the residue was chromatographed on silica with a 5-30% ethyl acetate-hexane gradient to give 50 mg of the title compound as a white solid (50 mg, 19%): mp 180-182° C.; 1H NMR (400 MHz, CDCl3) δ 8.16 (dd, J=6.2, 0.5 Hz, 1H), 7.54 (dd, J=8.7, 0.5 Hz, 1H), 5.07 (s, 2H), 4.00 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −105.64, −105.72, −137.68, −137.76; ESIMS m/z 341 ([M+H]+), 339 ([M−H]−).

Workup

dry with materialdried (Na2SO4)
customthe residue was chromatographed on silica with a 5-30% ethyl acetate-hexane gradient

Sources & evidence

ORD record: ord-40ff016877c74eddbd7bc6f356e6e824
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006250B2

Reaction notes

Loading…