Bis(trimethylsilyl)carbodiimide → N-(5'-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-ylidene)cyanamide

HRID 472999Notes

Reaction equation

HRID 472999 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]4([CH2:22][CH2:21][C:20]5[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=5[CH2:18][CH2:17]4)[C:14](=O)[C:13]=3[CH:28]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.C[Si]([N:33]=[C:34]=[N:35][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]4([CH2:22][CH2:21][C:20]5[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=5[CH2:18][CH2:17]4)[C:14](=[N:35][C:34]#[N:33])[C:13]=3[CH:28]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 581980625'-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-one

Product 1

HCID 86652173N-(5'-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-ylidene)cyanamide

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5′-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3′H-spiro[benzo[7]annulene-7,2′-benzofuran]-3′-one (0.0607 g, 0.155 mmol) in CH2Cl2 (5 mL) was added 0.7 mL of 1.0 M TiCl4 in CH2Cl2 at room temperature. After 1 h, 0.28 mL of bis(trimethylsilyl)carbodiimide was added to the red solution. The resulting mixture was then stirred at room temperature for 18 h. The mixture was quenched with ice, diluted with CH2Cl2, and dried over Na2SO4. After the solvent was removed under reduced pressure, the crude product was directly used in the next step without further purification.

Workup

  1. customThe mixture was quenched with ice
  2. additiondiluted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. customAfter the solvent was removed under reduced pressure
  5. customthe crude product was directly used in the next step without further purification

Sources & evidence

ORD record
ord-269813c5849d4856b657d11f7425a4d6
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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