Nitrogen → HCID 25139616, compound

HRID 1669191Notes

Reaction equation

N#N.Cl[C:4]1[N:5]=[N+:6]([O-:19])[C:7]2[C:16]3[CH2:15][N:14]([CH3:17])[CH2:13][CH2:12][C:11]=3[CH:10]=[CH:9][C:8]=2[N:18]=1.[Sn](CC)(CC)(CC)[CH2:21][CH3:22]>COCCOC.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>[CH2:21]([C:4]1[N:5]=[N+:6]([O-:19])[C:7]2[C:16]3[CH2:15][N:14]([CH3:17])[CH2:13][CH2:12][C:11]=3[CH:10]=[CH:9][C:8]=2[N:18]=1)[CH3:22]

Participants

Conditions

Temperature: 85 °C

Procedure

Pd(PPh3)4 (108 mg, 0.09 mmol) was added to a N2-purged, stirred solution of chloride 263 (225 mg, 0.9 mmol) and Et4Sn (0.36 mL, 1.8 mmol) in DME (15 mL) and the mixture was stirred at 85° C. for 18 h under N2. The solution was cooled to 20° C. and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (2-10%) of MeOH/DCM, to give 1-oxide 264 (130 mg, 60%) as a brown solid: mp 99-102° C.; 1H NMR δ 7.75 (d, J=8.6 Hz, 1H, H-5), 7.62 (d, J=8.6 Hz, 1H, H-6), 4.38 (s, 2H, H-10), 3.05-3.11 (m, 2H, H-7), 2.98 (q, J=7.6 Hz, 2H, CH2), 2.73 (t, J=5.9 Hz, 2H, H-8), 2.57 (s, 3H, NCH3), 1.42 (t, J=7.6 Hz, 3H, CH3); 13C NMR δ 167.1, 148.4, 137.1, 136.9, 136.3, 129.7, 126.1, 57.4, 50.5, 45.9, 30.7, 30.2, 12.2; MS (APCI) m/z (MH+, 100%). HRMS (FAB+) calcd for C13H17N4O (MH+) m/z 245.1402, found 245.1403.

Workup

custompurged
temperatureThe solution was cooled to 20° C.
customthe solvent evaporated
customThe residue was purified by chromatography
washeluting with a gradient (2-10%) of MeOH/DCM

Sources & evidence

ORD record: ord-cc304b78203e47ba81ca59850f3c17a1
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989451B2

Reaction notes

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