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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
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인쇄 미리보기

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HRID 634283 반응식
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]
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참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-52d510235fce40f6b49bc426e8587845
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321756B2

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