Iodine → 5-(3-iodo-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

HRID 634089노트

반응식

HRID 634089 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[O:14][C:13]([NH:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)=[N:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[I:25]I.[OH-].[K+].S(=O)(O)[O-].[Na+]>CN(C=O)C>[I:25][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]3[O:14][C:13]([NH:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)=[N:12][N:11]=3)[CH:5]=2)[NH:1][CH:2]=1

참가 물질

6

반응물 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 23665763Sodium BisulfiteHCID 867250885-(1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

생성물 1

HCID 867250895-(3-iodo-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine수율 59.44%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-(1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (28.0 g, 87.5 mmol) in DMF (270 mL) was added I2 (24.42 g, 96.25 mmol) followed by KOH (12.27 g, 218.75 mmol). The mixture was stirred at RT for 1 h, then poured into ice with 5% sodium bisulfite. The aqueous layer was extracted with DCM and the combined organic layers were washed with water, dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 2-3% MeOH in DCM) to give 5-(3-iodo-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (23.2 g, 52.0 mmol, 59.44%). MS (ESI, pos. ion) m/z: 447.0 (M+1); 1H-NMR (DMSO-d6) δ 11.87 (s, 1H), 8.22 (t, 1H), 7.69-7.65 (m, 2H), 7.44 (d, J=9 Hz, 2H), 7.34 (s, 1H), 6.92 (d, J=9 Hz, 2H), 5.76 (s, 1H), 4.38 (d, 2H), 3.73 (s, 3H).

후처리

  1. extractionThe aqueous layer was extracted with DCM
  2. washthe combined organic layers were washed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel chromatography (eluting with 2-3% MeOH in DCM)

출처 및 근거

ORD 기록
ord-f3d54a0fd54b4c969698894632d7f615
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321756B2

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