Phthalimide → 2-[(3-Chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-isoindole-1,3-dione

HRID 449023Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)O)=[N:4][CH:5]=[CH:6][N:7]=1.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[C:3]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[N:27]2[C:23](=[O:33])[C:24]3[C:25](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:26]2=[O:28])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of (3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methanol (12.0 g, 38.4 mmol), phthalimide (11.30 g, 76.8 mmol) and triphenylphosphine (20.10 g, 76.8 mmol) in THF (150 mL) in a flame-dried flask was added diisopropylazodicarboxylate (15.2 mL, 76.8 mmol) drop wise under nitrogen atmosphere. The reaction mixture was stirred at 60° C. for 16 h. TLC (EtOAc/Hexanes, 1:1) showed no starting material left. Solvent was then evaporated to give a crude residue which was purified through column on silica gel using EtOAc/Hexanes (1:1). Yield: 10.5 g (61%); 1H NMR (CDCl3, 300 MHz) δ 6.91 (s, 1H), 7.01-7.22 (m, 5H), 7.39-7.43 (m, 4H), 7.78-7.82 (m, 2H), 7.89-7.94 (m, 2H), 8.40 (d, J=2.4 Hz, 1H), 8.58 (d, J=2.4 Hz, 1H).

Workup

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customSolvent was then evaporated

Sources & evidence

ORD record: ord-a7d071da489d43c0b4bd3d2254fcb6e7
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481733B2

Reaction notes

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