Trimethylsilyl cyanide → (5-Fluoro-8-methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

HRID 1161442노트

반응식

HRID 1161442 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[N:3]=1.[F:14][C:15]1[C:24]([CH:25]=O)=[CH:23][C:22]([O:27][CH3:28])=[C:21]2[C:16]=1[CH2:17][CH2:18][CH2:19][O:20]2.C[Si]([C:33]#[N:34])(C)C.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>C1COCC1>[F:14][C:15]1[C:24]([CH:25]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([C:4]3[N:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[CH:8][CH:9]=2)[C:33]#[N:34])=[CH:23][C:22]([O:27][CH3:28])=[C:21]2[C:16]=1[CH2:17][CH2:18][CH2:19][O:20]2

참가 물질

6

반응물 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 595118625-Fluoro-8-methoxychroman-6-carboaldehyde

생성물 1

HCID 67097514(5-Fluoro-8-methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

After adding 940 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 1.125 g of 5-fluoro-8-methoxychromane-6-carbaldehyde, 1 g of MS3A and 1.43 ml of trimethylsilyl cyanide to a solution of 330 mg of Yb(OTf)3 in 20 ml of THF under a nitrogen atmosphere, the mixture was stirred overnight at room temperature. The reaction mixture was filtered through celite, and the celite was washed with ethyl acetate. The organic layer was concentrated under reduced pressure to give (5-fluoro-8-methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile (crude product).

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe celite was washed with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c852e18f3c4f4640a652e0394ee25d40
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816522B2

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