Bis(trimethylsilyl)carbodiimide → HCID 178511855, compound

HRID 1503401Notes

Reaction equation

HRID 1503401 reaction equation
[Br:1][C:2]1[CH:21]=[C:20]2[C:5]([CH2:6][C:7]3([C:19]2=O)[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:18])[C:13]=2[F:17])[CH2:8]3)=[CH:4][CH:3]=1.C[Si]([N:27]=[C:28]=[N:29][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:21]=[C:20]2[C:5](=[CH:4][CH:3]=1)[CH2:6][C:7]1([CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([F:18])[C:13]=3[F:17])[CH2:8]1)/[C:19]/2=[N:29]/[C:28]#[N:27]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 58197381HCID 58197381, compound

Product 1

HCID 178511855HCID 178511855, compoundYield 113.4%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-5′,6′-difluoro-3′,4′-dihydro-1′H-spiro[indene-2,2′-naphthalen]-1(3H)-one (150 mg, 0.41 mmol) in dried CH2Cl2 (1 mL) was added TiCl4 (1 M solution in DCM, 0.1.24 mmol) dropwise within 15 minutes, and stirred for 1 h. Then to this mixture was added bis-trimethlysilylcarbodiimide (234 mg, 1.24 mmol) dropwise. The resulting mixture was stirred overnight. The reaction mixture was poured into ice-water, extracted with CH2Cl2. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give (Z)—N-(5-bromo-5′,6′-difluoro-3′,4′-dihydro-1′H-spiro[indene-2,2′-naphthalene]-3(1H)-ylidene)cyanamide (180 mg, crude), which was used for the next step without further purification.

Workup

  1. stirringThe resulting mixture was stirred overnight
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b17b991016194eb4b697676852121a08
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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