Dibutyltin oxide → HCID 178437423, compound

HRID 885436Notes

Reaction equation

[C:1]([CH:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[CH:16]=[C:17]([CH2:20][N:21]3[C:25]4=[N:26][C:27]([CH3:31])=[CH:28][C:29]([CH3:30])=[C:24]4[N:23]=[C:22]3[CH2:32][CH3:33])[CH:18]=[CH:19][C:6]1=2)[CH3:4])#[N:2].C[Si]([N:38]=[N+:39]=[N-:40])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:32]([C:22]1[N:21]([CH2:20][C:17]2[CH:18]=[CH:19][C:6]3[N:5]([CH:3]([C:1]4[NH:40][N:39]=[N:38][N:2]=4)[CH3:4])[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[CH2:9][CH2:8][C:7]=3[CH:16]=2)[C:25]2=[N:26][C:27]([CH3:31])=[CH:28][C:29]([CH3:30])=[C:24]2[N:23]=1)[CH3:33]

Participants

Conditions

Temperature: 70 °C

Procedure

5-(1-Cyanoethyl)-2-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[b,f]azepine (520 mg, 1.19 mmol) obtained in step 1 of Example 19 was dissolved in toluene (12 mL), and the solution was added with trimethylsilylazide (2.54 mL, 19.1 mmol) and dibutyltinoxide (177 mg, 0.71 mmol), followed by stirring at 70° C. for 2 days. The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=25/1) to give the title compound (compound 22, 354 mg, 62%).

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (chloroform/methanol=25/1)

Sources & evidence

ORD record: ord-b55001a43cb34fee979ef0b3e9828bd3
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242151B2

Reaction notes

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