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2-Isopropoxy-6-(trimethylstannyl)pyrazine → 3-(3-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-methyl-1,2,4-oxadiazol-5-amine

HRID 634283
ノート
印刷プレビュー

反応式

HRID 634283 の反応式
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[C:14]([NH:16][CH3:17])[O:13][N:12]=3)[CH:9]=2)[N:4]([S:18]([C:21]2[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:3]=1.[CH:28]([O:31][C:32]1[CH:37]=[N:36][CH:35]=[C:34]([Sn](C)(C)C)[N:33]=1)([CH3:30])[CH3:29]>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:28]([O:31][C:32]1[N:33]=[C:34]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]4[N:15]=[C:14]([NH:16][CH3:17])[O:13][N:12]=4)[CH:9]=3)[N:4]([S:18]([C:21]3[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=3)(=[O:19])=[O:20])[CH:3]=2)[CH:35]=[N:36][CH:37]=1)([CH3:30])[CH3:29]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 683280402-Isopropoxy-6-(trimethylstannyl)pyrazineHCID 867251173-(3-iodo-1-tosyl-1H-indol-5-yl)-N-methyl-1,2,4-oxadiazol-5-amine

生成物 1

HCID 683281653-(3-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-methyl-1,2,4-oxadiazol-5-amine収率 31.7%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 178418397
HCID 178418397、化合物
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

Argon gas was bubbled through a solution of 3-(3-iodo-1-tosyl-1H-indol-5-yl)-N-methyl-1,2,4-oxadiazol-5-amine (250 mg, 0.50 mmol) and 2-isopropoxy-6-(trimethylstannyl)-pyrazine (168 mg, 0.55 mmol) in dry DMF (2.5 mL) for 15 min. To the mixture was added CuI (95 mg, 0.50 mmol) and Pd(PPh3)4 (59 mg, 0.050 mmol) and argon gas was further bubbled for additional 15 min. The reaction was heated at 90° C. for 1 h then cooled to RT. The reaction was quenched with ice cold water. The resulting suspension was filtered and washed with H2O. The solid was purified with basic alumina column chromatography (eluent: 20% EtOAc in petroleum ether) to give 3-(3-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-methyl-1,2,4-oxadiazol-5-amine (80 mg, 31.5%). MS (ESI, pos. ion) m/z: 505.1 (M+1).

後処理

  1. customwas further bubbled for additional 15 min
  2. temperaturethen cooled to RT
  3. customThe reaction was quenched with ice cold water
  4. filtrationThe resulting suspension was filtered
  5. washwashed with H2O
  6. customThe solid was purified with basic alumina column chromatography (eluent: 20% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-52d510235fce40f6b49bc426e8587845
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321756B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート