Phthalimide → 2-(1-{5-[5-(4-isopropoxyphenoxy)-1,3,4-thiadiazol-2-yl]thien-2-yl}ethyl)-1H-isoindole-1,3(2H)-dione

HRID 404891ノート

反応式

HRID 404891 の反応式
[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:14][C:13]([C:15]3[S:19][C:18]([CH:20](O)[CH3:21])=[CH:17][CH:16]=3)=[N:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[C:25]1(=[O:35])[NH:29][C:28](=[O:30])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:14][C:13]([C:15]3[S:19][C:18]([CH:20]([N:29]4[C:25](=[O:35])[C:26]5[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=5)[C:28]4=[O:30])[CH3:21])=[CH:17][CH:16]=3)=[N:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 694341721-{5-[5-(4-Isopropoxyphenoxy)-1,3,4-thiadiazol-2-yl]thien-2-yl}ethanol

生成物 1

HCID 694368152-(1-{5-[5-(4-isopropoxyphenoxy)-1,3,4-thiadiazol-2-yl]thien-2-yl}ethyl)-1H-isoindole-1,3(2H)-dione収率 277.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

A solution of Example 24E (0.37 g, 1.025 mmol), phthalimide (0.151 g, 1.025 mmol), and triphenyl phosphine (0.537 g, 2.05 mmol) in tetrahydrofuran (5 mL) was treated with diisopropyl azodicarboxylate (0.385 mL, 1.85 mmol) and the resulting solution was stirred at 25° C. for 3 hours. The reaction was concentrated under reduced pressure on a rotary evaporator to provide 1.4 g of a yellow oil. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 1% to 20% ethyl acetate in hexanes to provide 0.49 g (98%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.76-7.98 (m, 4H) 7.51 (d, J=3.68 Hz, 1H) 7.38 (d, J=9.19 Hz, 2H) 7.14 (dd, J=3.68, 0.92 Hz, 1H) 7.01 (d, J=9.19 Hz, 2H) 5.60-5.77 (m, 1H) 4.55-4.70 (m, 1H) 1.88 (d, J=7.35 Hz, 3H) 1.27 (d, J=5.88 Hz, 6H); MS (ESI) m/z 492 (M+H)+.

後処理

  1. concentrationThe reaction was concentrated under reduced pressure on a rotary evaporator

出典と根拠

ORDレコード
ord-15fb4ba0bf234db593ac608364e8be38
出典データセット
uspto-grants-2014_06
特許番号
US08748627B2

反応ノート

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