Potassium Iodide → (1-Benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulen-6-yl)-phenyl-methanone

HRID 220783Notes

Reaction equation

[H-].[Na+].[C:3]([N:11]1[CH2:20][CH2:19][C:18]2[N:17]=[C:16]([CH3:21])[NH:15][C:14]=2[C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]1=2)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[I-].[K+]>C1COCC1>[CH2:26]([N:15]1[C:14]2[C:13]3[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=3[N:11]([C:3]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)=[O:10])[CH2:20][CH2:19][C:18]=2[N:17]=[C:16]1[CH3:21])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60% dispersion in oil, 905 mg, 22.5 mmol) was placed in anhydrous THF (200 ml) and cooled down to 0° C. 6-Benzoyl-2-methyl-1,4,5,6-tetrahydro-1,3,6-triaza-benzo[e]azulene from Example E5.8 (4.9 g, 16.1 mmol) was added dropwise and the mixture was stirred for 1 h at room temperature. Benzyl bromide (2.31 ml, 19.3 mmol) and potassium iodide (1.34 g, 8.0 mmol) were added and the mixture was stirred for 16 h. The solution was diluted with EtOAC, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; EtOAc) to yield the title compound (5.73 g, 90%).

Workup

stirringthe mixture was stirred for 16 h
additionThe solution was diluted with EtOAC
washwashed with saturated NaHCO3
dry with materialbrine, dried
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (eluant; EtOAc)

Sources & evidence

ORD record: ord-3b2e528c7b67401f983f1b1af7ec7833
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202858B2

Reaction notes

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