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

HRID 634089ノート

反応式

HRID 634089 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f3d54a0fd54b4c969698894632d7f615
出典データセット
uspto-grants-2016_04
特許番号
US09321756B2

反応ノート

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