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Water → 2-(3-(6-isopropoxypyridin-2-yl)-1H-indol-5-yl)-5-methyl-1,3,4-oxadiazole

HRID 634198
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HRID 634198 반응식
[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[O:21][C:22]([CH3:25])=[N:23][N:24]=4)[CH:18]=3)[N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH:12]=2)[CH:8]=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].O>CO.C1COCC1>[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[O:21][C:22]([CH3:25])=[N:23][N:24]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[CH:7][CH:6]=1)([CH3:3])[CH3:2]
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참가 물질

6

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HCID 962WaterHCID 10796Cesium carbonateHCID 683285952-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-5-methyl-1,3,4-oxadiazole

생성물 1

HCID 683287522-(3-(6-isopropoxypyridin-2-yl)-1H-indol-5-yl)-5-methyl-1,3,4-oxadiazole수율 22.9%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 8028
Tetrahydrofuran
용매

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온도
45 °C

실험 절차

2-(3-(6-Isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-5-methyl-1,3,4-oxadiazole (214 mg, 0.438 mmol) in a round bottomed flask was dissolved in MeOH (1.500 mL) and THF (3.0 mL). Cesium carbonate (428 mg, 1.314 mmol) (Aldrich) was added, the flask was fitted with a reflux condenser and the contents of the flask were heated at 45° C. for 15 min. H2O (30 mL) was added and the mixture was extracted with EtOAc (2×75 mL). The combined organic layers were dried, filtered and concentrated. The residue was purified with RP-HPLC (10-90% MeCN in H2O with 0.01% TFA as additive) to give 2-(3-(6-isopropoxypyridin-2-yl)-1H-indol-5-yl)-5-methyl-1,3,4-oxadiazole (33.6 mg, 11.1%). MS (ESI, pos. ion) m/z 335.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 11.89 (br. s., 1H), 9.20-9.29 (m, 1H), 8.25 (d, J=2.5 Hz, 1H), 7.82 (dd, J=8.5, 1.7 Hz, 1H), 7.57-7.72 (m, 2H), 7.46 (d, J=7.4 Hz, 1H), 6.53 (d, J=8.0 Hz, 1H), 5.58 (dt, J=12.3, 6.2 Hz, 1H), 2.59 (s, 3H), 1.47 (d, J=6.1 Hz, 6H).

후처리

  1. customthe flask was fitted with a reflux condenser
  2. extractionthe mixture was extracted with EtOAc (2×75 mL)
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with RP-HPLC (10-90% MeCN in H2O with 0.01% TFA as additive)

출처 및 근거

ORD 기록
ord-a3f8b8bd07c24ba2aee55a978da2791d
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321756B2

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