[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:17][CH2:16][C:15]4[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=4[CH2:13][CH2:12]3)[C:8]2=O)=[CH:4][CH:3]=1.[C:22](=[N:28][Si](C)(C)C)=[N:23][Si](C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[CH2:6][C:7]1([CH2:17][CH2:16][C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[CH2:13][CH2:12]1)/[C:8]/2=[N:28]/[C:22]#[N:23]To a solution of 6′-bromo-5,6,8,9-tetrahydrospiro[benzo[7]annulene-7,2′-inden]-1′(3′H)-one (20 mg, 0.059 mmol) in DCM (2 mL) was added TiCl4 (44.7 mg, 0.235 mmol) dropwise, the mixture was stirred at 50° C. at Ar2 under microwave for 20 minutes, N,N′-methanediylidenebis(1,1,1-trimethylsilanamine) (43.8 mg, 0.235 mmol) was added dropwise. The mixture was stirred at 60° C. at Ar2 under microwave for 10 minutes and repeated the same operation for one time and then poured into ice-water (10 mL). The aqueous layer was extracted with CH2Cl2, which was combined with the organic layer. The organic layer was dried and concentrated to give crude (Z)—N-(5′-bromo-5,6,8,9-tetrahydrospiro[benzo[7]annulene-7,2′-indene]-3′(1′H)-ylidene)cyanamide (20 mg, 4%).
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