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

HRID 1408709ノート

反応式

HRID 1408709 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ed31cd62eece4acfb07a2735aa7feb61
出典データセット
uspto-grants-2014_12
特許番号
US08921359B2

反応ノート

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