Bis(trimethylsilyl)carbodiimide → N-(5'-(3-cyanophenyl)-5,7,8,9-tetrahydrospiro[benzo[7]annulene-6,2'-indene]-3'(1'H)-ylidene)cyanamide

HRID 472979Notes

Reaction equation

O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])[CH:9]=2)[CH2:4][C:3]21[CH2:24][CH2:23][CH2:22][C:21]1[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=1[CH2:19]2.C[Si]([N:33]=[C:34]=[N:35][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:14]([C:13]1[CH:12]=[C:11]([C:8]2[CH:7]=[C:6]3[C:5](=[CH:10][CH:9]=2)[CH2:4][C:3]2([CH2:19][CH2:20][CH2:28][C:27]4[CH:23]=[CH:22][CH:21]=[CH:25][C:26]=4[CH2:2]2)[C:24]3=[N:35][C:34]#[N:33])[CH:18]=[CH:17][CH:16]=1)#[N:15]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-(1′-oxo-1′,3′,5,7,8,9-hexahydrospiro[benzo[7]annulene-6,2′-indene]-6′-yl)benzonitrile (31 mg, 0.086 mmol) in CH2Cl2 (2 mL) was added TiCl4 (66 mg). It was stirred in microwave at 50° C. for 5 minutes. Then bis-trimethylsilylcarbodiimide (112 mg, 0.6 mmol) was added. The resulting mixture was stirred in microwave at 60° C. for 10 minutes. The reaction mixture was poured into ice-water, extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to give N-(5′-(3-cyanophenyl)-5,7,8,9-tetrahydrospiro[benzo[7]annulene-6,2′-indene]-3′(1′H)-ylidene)cyanamide (50 mg, crude).

Workup

stirringThe resulting mixture was stirred in microwave at 60° C. for 10 minutes
extractionextracted with DCM
dry with materialThe combined organic phases were dried over anhydrous Na2SO4
filtrationfiltered
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-dbd19b0c13124bc1b25d5e2cec9d2c89
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633212B2

Reaction notes

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