Phthalimide → 2-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)-1h-isoindole-1,3(2h)-dione

HRID 404870ノート

反応式

HRID 404870 の反応式
[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([CH:20](O)[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=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(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([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)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 694373051-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethanol

生成物 1

HCID 694391172-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)-1h-isoindole-1,3(2h)-dione収率 49.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of Example 3B (314 mg, 0.87 mmol), phthalimide (140 mg, 0.95 mmol) and triphenylphophine (341 mg, 1.3 mmol) in tetrahydrofuran (25 mL), at room temperature was slowly added diethyl azodicarboxylate (205 uL, 1.3 mmol). The reaction mixture was stirred at room temperature, overnight. The solvent was removed under vacuum and the product was purified on a silica-gel column using a gradient of 10-15% ethyl acetate in hexane and yielded the product as white powder (210 mg). 1H NMR (300 MHz, CDCl3) δ ppm 7.63-7.97 (m, 5H) 7.12-7.24 (m, 2H) 7.00 (d, J=3.68 Hz, 1H) 6.81-6.96 (m, 3H) 5.73 (q, J=7.35 Hz, 1H) 4.44-4.59 (heptet, J=6.25 Hz, 1H) 196 (d, J=7.35 Hz, 3H) 1.34 (d, J=6.25 Hz, 6H), MS (DCI): m/z 491 (M+H).

後処理

  1. customat room temperature
  2. customThe solvent was removed under vacuum
  3. customthe product was purified on a silica-gel column

出典と根拠

ORDレコード
ord-16cdefc5966c425890489ae154d162ca
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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