Phthalimide → HCID 90461968, compound

HRID 588791Notes

Reaction equation

HRID 588791 reaction equation
[Cl:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([O:6][C:7]2[CH:12]=[C:11]([O:13][CH2:14][CH2:15]O)[CH:10]=[CH:9][N:8]=2)=[C:4]([I:20])[CH:3]=1.[C:21]1(=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](=[O:30])[NH:22]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([O:6][C:7]2[CH:12]=[C:11]([O:13][CH2:14][CH2:15][N:22]3[C:23](=[O:30])[C:24]4[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:21]3=[O:31])[CH:10]=[CH:9][N:8]=2)=[C:4]([I:20])[CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 117607156HCID 117607156, compound

Product 1

HCID 90461968HCID 90461968, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(2-(4,5-dichloro-2-iodophenoxy)pyridin-4-yloxy)ethanol (130 mg, 0.31 mmol), isoindoline-1,3-dione (54 mg, 0.37 mmol), PPh3 (160 mg, 0.61 mmol) in THF (5 mL) at 0° C., DIAD (123 mg, 0.61 mmol) was added. The resulting mixture was allowed to warm to room temperature and stirred for 15 h. The mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1 to 5:1) to afford the desired product (120 mg, 71% yield). ESI-MS m/z: 555.0[M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1 to 5:1)

Sources & evidence

ORD record
ord-0317cada9178428eb4100ae6dbf068a7
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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