T0400-2412 → HCID 68946361, compound

HRID 1967708Notes

Reaction equation

HRID 1967708 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.[Br-].[Cl:24][C:25]1[CH:50]=[CH:49][C:28]([CH2:29][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:27][CH:26]=1>>[Cl:24][C:25]1[CH:26]=[CH:27][C:28](/[CH:29]=[CH:18]/[C:17]2[CH:16]=[C:15]([CH2:14][CH2:13][CH2:12][N:3]3[C:4](=[O:11])[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:2]3=[O:1])[CH:22]=[CH:21][CH:20]=2)=[CH:49][CH:50]=1.[Cl:24][C:25]1[CH:26]=[CH:27][C:28](/[CH:29]=[CH:18]\[C:17]2[CH:16]=[C:15]([CH2:14][CH2:13][CH2:12][N:3]3[C:4](=[O:11])[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:2]3=[O:1])[CH:22]=[CH:21][CH:20]=2)=[CH:49][CH:50]=1

Participants

4

Reactant 2

HCID 11102709T0400-2412HCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde

Product 2

HCID 68942767HCID 68942767, compoundYield 10%HCID 68946361HCID 68946361, compoundYield 13%

Procedure

Phthalimide 29 was coupled with (4-chlorobenzyl)triphenylphosphonium bromide according to the method used in Example 76. Purification by flash chromatography (7% EtOAc-hexanes) gave (E)-2-(3-(3-(4-chlorostyryl)phenyl)propyl)isoindoline-1,3-dione (0.120 g, 10%) and (Z)-2-(3-(3-(4-chlorostyryl)phenyl)propyl)isoindoline-1,3-dione (0.150 g, 13%) as yellow solids. Cis-isomer: 1H NMR (400 MHz, CDCl3) δ 7.79-7.86 (m, 2H), 7.68-7.73 (m, 3H), 7.12-7.17 (m, 5H), 7.00-7.05 (m, 3H), 6.58 (d, J=12.0 Hz, 1H), 6.50 (d, J=12.0 Hz, 1H), 3.68 (t, J=7.2 Hz, 2H), 2.60 (t, J=7.6 Hz, 2H), 1.90-1.97 (m, 2H).

Workup

  1. customPurification by flash chromatography (7% EtOAc-hexanes)

Sources & evidence

ORD record
ord-3c8944d920694866b5795fb16ea2c0d1
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Reaction notes

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