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

HRID 634286
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인쇄 미리보기

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HRID 634286 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][CH:17]([CH3:19])[CH3:18])[O:13][N:12]=3)[CH:9]=2)[N:4]([S:20]([C:23]2[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:3]=1.[CH:30]([O:33][C:34]1[CH:39]=[N:38][CH:37]=[C:36]([Sn](C)(C)C)[N:35]=1)([CH3:32])[CH3:31]>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:30]([O:33][C:34]1[N:35]=[C:36]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]4[N:15]=[C:14]([NH:16][CH:17]([CH3:18])[CH3:19])[O:13][N:12]=4)[CH:9]=3)[N:4]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:21])=[O:22])[CH:3]=2)[CH:37]=[N:38][CH:39]=1)([CH3:32])[CH3:31]
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참가 물질

6

반응물 2

HCID 683280402-Isopropoxy-6-(trimethylstannyl)pyrazineHCID 683287503-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,2,4-oxadiazol-5-amine

생성물 1

HCID 683287123-(3-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,2,4-oxadiazol-5-amine수율 43.7%

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-isopropyl-1,2,4-oxadiazol-5-amine (450 mg, 0.86 mmol) and 2-isopropoxy-6-(trimethylstannyl)pyrazine (311 mg, 1.03 mmol) in dry DMF (4.5 ml) for 15 min. To the mixture was added CuI (163 mg, 0.86 mmol) and Pd(PPh3)4 (99 mg, 0.086 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 water. 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-isopropyl-1,2,4-oxadiazol-5-amine (200 mg, 43.5%). MS (ESI, pos. ion) m/z: 533.3 (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 water
  6. customThe solid was purified with basic alumina column chromatography (eluent: 20% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-deda81e4034e4a0e942851c42cd673c4
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321756B2

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