Nitrogen → HCID 25140184, compound

HRID 1669188Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

Pd(PPh3)4 (350 mg, 0.3 mmol) was added to a N2-purged, stirred solution of chloride 257 (750 mg, 3.0 mmol) and Et4Sn (1.2 mL, 6.0 mmol) in DME (35 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 (2-5%) of MeOH/DCM, to give 1-oxide 260 (590 mg, 81%) as a brown solid: mp 129-131° C.; 1H NMR δ 8.21 (s, 1H, H-10), 7.63 (s, 1H, H-5), 3.79 (s, 2H, H-6), 3.16 (t, J=6.0 Hz, 2H, H-8), 3.02 (q, J=7.6 Hz, 2H, CH2), 2.77 (t, J=6.0 Hz, 2H, H-9), 2.51 (s, 3H, NCH3), 1.43 (t, J=7.6 Hz, 3H, CH3); 13C NMR δ 167.3, 145.8144.6, 138.2, 131.7, 125.0, 118.8, 58.1, 52.3, 45.9, 30.7, 29.6, 12.2; MS (APCI) m/z 245 (MH+, 100%). Anal. calcd for C13H16N4O.¼H2O: C, 62.5; H, 6.7; N, 22.4. Found: C, 62.6; H, 6.6; N, 22.4%.

Workup

custompurged
temperatureThe solution was cooled to 20° C.
customthe solvent evaporated
customThe residue was purified by chromatography
washeluting with a gradient (2-5%) of MeOH/DCM

Sources & evidence

ORD record: ord-788bcf107b884e80ba164f4192080f28
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989451B2

Reaction notes

Loading…