Dibutyltin oxide → HCID 178439871, compound

HRID 452129Notes

Reaction equation

[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:27]=[CH:26][C:13]3/[C:14](=[CH:23]/[C:24]#[N:25])/[C:15]4[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=4[CH2:17][CH2:18][C:12]=3[CH:11]=2)[C:7]2[CH:28]=[CH:29][CH:30]=[CH:31][C:6]=2[N:5]=1)[CH2:2][CH3:3].C[Si]([N:36]=[N+:37]=[N-:38])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:27]=[CH:26][C:13]3/[C:14](=[CH:23]/[C:24]4[NH:38][N:37]=[N:36][N:25]=4)/[C:15]4[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=4[CH2:17][CH2:18][C:12]=3[CH:11]=2)[C:7]2[CH:28]=[CH:29][CH:30]=[CH:31][C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 90 °C

Procedure

(E)-[2-(2-Propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (200 mg, 0.496 mmol) obtained in Example 1 was dissolved in toluene (5 mL), trimethylsilylazide (1.3 mL, 9.92 mmol) and dibutyltin oxide (123 mg, 0.496 mmol) were added, and the mixture was stirred at 90° C. for 24 hr. The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=99/1) to give the title compound (compound 4) (111 mg, 50%).

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (chloroform/methanol=99/1)

Sources & evidence

ORD record: ord-4f087321809f4f2598abc887c8a734db
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486980B2

Reaction notes

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