Nitrogen → 5-(3-(4-chloropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

HRID 634101노트

반응식

HRID 634101 반응식
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:15][C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[N:13][N:12]=3)[CH:9]=2)[N:4]([S:26]([C:29]2[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH:3]=1.[Cl:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39]([Sn](CCCC)(CCCC)CCCC)[N:38]=1.N#N>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>[Cl:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]4[O:15][C:14]([NH:16][CH2:17][C:18]5[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=5)=[N:13][N:12]=4)[CH:9]=3)[N:4]([S:26]([C:29]3[CH:30]=[CH:31][C:32]([CH3:33])=[CH:34][CH:35]=3)(=[O:27])=[O:28])[CH:3]=2)[N:38]=1

참가 물질

7

반응물 3

HCID 947Nitrogen2회HCID 149763044-Chloro-2-(tributylstannyl)pyrimidineHCID 683283255-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

생성물 1

HCID 867250935-(3-(4-chloropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine수율 53.3%

시약·촉매·용매 3

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

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온도
80 °C

실험 절차

A solution of 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (3.0 g, 5.20 mmol) and 4-chloro-2-(tributylstannyl)pyrimidine (2.5 g, 6.00 mmol) in DMF was bubbled with N2 for 15 min. To the above mixture was added CuI (476 mg; 2.50 mmol) and Pd(PPh3)4 (577 mg, 0.52 mmol) and N2 gas was bubbled for another 15 min. The reaction was heated at 80° C. for 1 h. The reaction was quenched with H2O and the resulting precipitate was filtered, washed with H2O and dried. The crude material was purified with silica gel chromatography (eluting with 30% EtOAc in Hex) to give 5-(3-(4-chloropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (1.6 g, 53.3%). MS (ESI, pos. ion) m/z: 586.6 (M+1); 1H-NMR (400 MHz, DMSO-d6): δ 8.96 (s, 1H), 8.91 (d, J=4 Hz, 1H), 8.62 (s, 1H), 8.35 (m, 1H), 8.17 (d, J=8 Hz, 1H), 8.10 (d, J=8 Hz, 2H), 7.91 (d, J=8 Hz, 1H), 7.65-7.62 (m, 2H), 7.45-7.43 (m, 6H), 7.33 (d, J=8 Hz, 2H), 6.90 (d, J=8 Hz, 2H), 4.38 (d, J=5.6 Hz, 2H), 3.72 (s, 3H), 2.33 (s, 3H).

후처리

  1. customwas bubbled for another 15 min
  2. customThe reaction was quenched with H2O
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with H2O
  5. customdried
  6. customThe crude material was purified with silica gel chromatography (eluting with 30% EtOAc in Hex)

출처 및 근거

ORD 기록
ord-2edc13146d2f4260bcfd0538f1dea4e2
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321756B2

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