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

HRID 404870Notes

Reaction equation

HRID 404870 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-16cdefc5966c425890489ae154d162ca
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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