Bis(trimethylsilyl)carbodiimide → 7-Fluoro-6-(2-fluoro-pyridin-3-yl)-2-phenylchroman-4-ylidene-cyanamide

HRID 2096521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2096521
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH2:7][CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9]2)=[CH:4][C:3]=1[C:19]1[C:20]([F:25])=[N:21][CH:22]=[CH:23][CH:24]=1.C[Si]([N:30]=[C:31]=[N:32][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[N:32][C:31]#[N:30])[CH2:7][CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9]2)=[CH:4][C:3]=1[C:19]1[C:20]([F:25])=[N:21][CH:22]=[CH:23][CH:24]=1

Komponenten

5

Edukt 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 584240177-Fluoro-6-(2-fluoropyridin-3-yl)-2-phenylchroman-4-one

Produkt 1

HCID 866574407-Fluoro-6-(2-fluoro-pyridin-3-yl)-2-phenylchroman-4-ylidene-cyanamideAusbeute 120,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 7-fluoro-6-(2-fluoropyridin-3-yl)-2-phenylchroman-4-one (78 mg, 0.23 mmol) in CH2Cl2 (5 mL) under N2 was added TiCl4 (1 M solution in DCM, 1.15 mL, 1.15 mmol) dropwise within 15 minutes at room temperature under dark. After addition, the reaction mixture was stirred for 1 h. To this mixture was added bis-trimethylsilylcarbodiimide (94.3 mg, 0.506 mmol) dropwise. The resulting mixture was stirred overnight. The reaction mixture was poured into ice-water and extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to give 7-fluoro-6-(2-fluoro-pyridin-3-yl)-2-phenylchroman-4-ylidene-cyanamide (100 mg, 100%).

Aufarbeitung

  1. additionAfter addition
  2. stirringThe resulting mixture was stirred overnight
  3. extractionextracted with DCM
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-1178440bfd67487f83d90760f6f73d78
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450308B2

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