Nitrogen → 7-(Dimethylamino)-3-ethyl-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

HRID 1669098Notes

Reaction equation

N#N.Cl[C:4]1[N:5]=[N+:6]([O-:20])[C:7]2[CH:16]=[C:15]3[C:11]([CH2:12][CH:13]([N:17]([CH3:19])[CH3:18])[CH2:14]3)=[CH:10][C:8]=2[N:9]=1.[Sn](CC)(CC)(CC)[CH2:22][CH3:23]>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>[CH3:18][N:17]([CH3:19])[CH:13]1[CH2:12][C:11]2[C:15](=[CH:16][C:7]3[N+:6]([O-:20])=[N:5][C:4]([CH2:22][CH3:23])=[N:9][C:8]=3[CH:10]=2)[CH2:14]1

Participants

Conditions

Temperature: 85 °C

Procedure

Pd(PPh3)4 (240 mg, 0.21 mmol) was added to a N2-purged, stirred solution of chloride 112 (550 mg, 1.9 mmol) and SnEt4 (800 mg, 3.4 mmol) in DME (55 mL), and the mixture stirred at 85° C. under N2 for 16 h. The mixture was cooled, the solvent evaporated and the residue purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1-oxide 115 (250 mg, 47%) as an unstable brown solid: 1H NMR δ 8.23 (s, 1H, H-9), 7.73 (s, 1H, H-5), 3.04-3.33 (m, 5H, H-6, H-7, H-8) 3.02 (q, J=7.6 Hz, 2H, CH2), 2.35 [s, 6H, N(CH3)2], 1.43 (t, J=7.6 Hz, 3H, CH3); 13C NMR δ 167.2, 152.2, 147.6, 146.3, 132.4, 122.9, 114.6, 67.6, 43.8 (2), 38.0, 37.6, 30.6, 12.3; HRMS calcd for C14H18N4O (M+) m/z 258.1481, found 258.1473.

Workup

custompurged
temperatureThe mixture was cooled
customthe solvent evaporated
customthe residue purified by chromatography
washeluting with a gradient (0-10%) of MeOH/DCM

Sources & evidence

ORD record: ord-c30d7636ff914adba6072e1a47e58e66
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989451B2

Reaction notes

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