Triphenylphosphine → HCID 67189743, compound

HRID 546084Notes

Reaction equation

O[CH2:2][C:3]#[C:4][CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].[N+:17]([C:20]1[CH:24]=[CH:23][NH:22][N:21]=1)([O-:19])=[O:18].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>[N+:17]([C:20]1[CH:24]=[CH:23][N:22]([CH2:2][C:3]#[C:4][CH2:5][N:6]2[C:14](=[O:15])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])[N:21]=1)([O-:19])=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

The 2-(4-hydroxy-but-2-ynyl)-isoindole-1,3-dione (1.29 g, 6.00 mmol), 3-Nitro-1H-pyrazole (prepared in example 3, 655 mg, 5.80 mmol) and triphenylphosphine (1.57 g, 6.00 mmol) were combined and dissolved in tetrahydrofuran (30 mL) and then chilled to 0° C. While stirring, diisopropyl azodicarboxylate (1.77 mL, 9 mmol) was added dropwise. The ice bath was removed and the reaction continued to stir at 25° C. for 1 h. At this point the desired product had precipitated. Collection of the precipitate using in vacuo filtration followed by rinsing with tetrahydrofuran (2×10 mL) then drying in vacuo for 2 h afforded 2-[4-(3-nitro-pyrazol-1-yl)-but-2-ynyl]-isoindole-1,3-dione (1.54 g, 86%) as a white powder: ESI-LRMS m/e calcd for C15H10N4O4 [M+] 310.07. found 311.17 [M+H+], 621.20 [2M+H+].

Workup

customThe ice bath was removed
stirringto stir at 25° C. for 1 h
customAt this point the desired product had precipitated
customCollection of the precipitate
filtrationusing in vacuo filtration
washby rinsing with tetrahydrofuran (2×10 mL)
customthen drying in vacuo for 2 h

Sources & evidence

ORD record: ord-d600083377194f7a9a0f2919beb01674
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935699B2

Reaction notes

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