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

HRID 404891Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 25 °C

Procedure

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)+.

Workup

concentrationThe reaction was concentrated under reduced pressure on a rotary evaporator

Sources & evidence

ORD record: ord-15fb4ba0bf234db593ac608364e8be38
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748627B2

Reaction notes

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