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

HRID 1698665

반응식

HRID 1698665 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.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:26]=O)[CH:19]=[C:20]2[C:25]=1[O:24][CH2:23][CH2:22][CH2:21]2.C[Si]([C:32]#[N:33])(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]>ClCCl>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:26]([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:32]#[N:33])[CH:19]=[C:20]2[C:25]=1[O:24][CH2:23][CH2:22][CH2:21]2

참가 물질

6

반응물 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 128319838-Methoxychromane-6-carbaldehydeHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline

생성물 1

HCID 67097438(8-Methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

After adding 700 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 770 mg of 8-methoxychromane-6-carbaldehyde [CAS No. 81258-23-3], 1 g of MS3A and 1.1 ml of trimethylsilyl cyanide to a solution of 250 mg of Yb(OTf)3 in 5 ml of dichloromethane 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 100 ml of ethyl acetate. The organic layer was concentrated under reduced pressure to give a crude product of (8-methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile.

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe celite was washed with 100 ml of ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-72202eace7bb4f4284da39978a7dbac8
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163787B2

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