Bis(trimethylsilyl)carbodiimide → N-(5-(3-cyanophenyl)-2',3',5',6'-tetrahydrospiro[indene-1,4'-pyran]-3(2H)-ylidene)cyanamide

HRID 472962Notes

Reaction equation

HRID 472962 reaction equation
O=[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=3)[C:19]#[N:20])[CH:14]=2)[C:4]2([CH2:9][CH2:8][O:7][CH2:6][CH2:5]2)[CH2:3]1.C[Si]([N:28]=[C:29]=[N:30][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:19]([C:18]1[CH:17]=[C:16]([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[C:4]2([CH2:5][CH2:6][O:7][CH2:8][CH2:9]2)[CH2:3][C:2]3=[N:30][C:29]#[N:28])[CH:23]=[CH:22][CH:21]=1)#[N:20]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 665847103-(3-Oxo-2,2',3,3',5',6'-hexahydrospiro[indene-1,4'-pyran]-5-yl)benzonitrile

Product 1

HCID 86652169N-(5-(3-cyanophenyl)-2',3',5',6'-tetrahydrospiro[indene-1,4'-pyran]-3(2H)-ylidene)cyanamide

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-oxo-2,2′,3,3′,5′,6′-hexahydrospiro[indene-1,4′-pyran]-5-yl)benzonitrile (42 mg, 0.139 mmol) in anhydrous DCM (10 mL) under N2 atmosphere was added 1 M TiCl4 (in DCM, 0.28 mL, 0.28 mmol) dropwise within 15 min at room temperature. It was stirred another 1 h after the addition. To this mixture was added Bis-trimethylsilylcarbodiimide (0.1 mL, 0.427 mmol) dropwise. The resulting mixture was stirred overnight. The reaction mixture was quenched with ice-water (15 g), and stirred for 30 min, then it was transferred to a separating funnel, the separated aqueous phase was extracted 2 times with DCM. The combined organic phases were dried over anhydrous Na2SO4, and filtered, and concentrated to give the desired product as white solid, which was used for next step without further purification. MS ESI+ve m/z 328 (M+H)+.

Workup

  1. additionafter the addition
  2. stirringThe resulting mixture was stirred overnight
  3. customThe reaction mixture was quenched with ice-water (15 g)
  4. stirringstirred for 30 min
  5. customit was transferred to a separating funnel
  6. extractionthe separated aqueous phase was extracted 2 times with DCM
  7. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-92cada9f46834cf89bc5f3998732d7af
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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