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

HRID 1408709노트

반응식

HRID 1408709 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 866574407-Fluoro-6-(2-fluoro-pyridin-3-yl)-2-phenylchroman-4-ylidene-cyanamide수율 120.3%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

실험 절차

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-phenyl-chroman-4-ylidene-cyanamide (100 mg, 100%).

후처리

  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

출처 및 근거

ORD 기록
ord-ed31cd62eece4acfb07a2735aa7feb61
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921359B2

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