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

HRID 1698665

反応式

HRID 1698665 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-72202eace7bb4f4284da39978a7dbac8
出典データセット
uspto-grants-2012_04
特許番号
US08163787B2

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