Toluene → 2-((2-Ethyl-2H-indazol-5-yl)methyl)isoindoline-1,3-dione

HRID 73078Notes

Reaction equation

[CH2:1]([N:3]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12]O)=[CH:9]2)=[N:4]1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33]1(=[O:43])[NH:37][C:36](=[O:38])[C:35]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:34]12.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>C1COCC1>[CH2:1]([N:3]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][N:37]3[C:33](=[O:43])[C:34]4[C:35](=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:36]3=[O:38])=[CH:9]2)=[N:4]1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2-ethyl-2H-indazol-5-yl)methanol (step-2 of Example 13, 132 mg, 0.75 mmol) in THF (10 mL) was added triphenylphosphine (236 mg, 0.90 mmol) and phthalimide (132 mg, 0.90 mmol). The mixture was cooled to 0° C. Then, to the mixture was added 40% DEAD in toluene (0.30 mL, 0.75 mmol) and allowed to warm up to room temperature. The mixture was stirred at room temperature for 4 hrs. The reaction mixture was evaporated. The residual oil was purified by silica gel column chromatography (0-50% EtOAc in hexane) to give the titled compound as a mixture. The mixture was used next step without further purification.

Workup

temperatureto warm up to room temperature
customThe reaction mixture was evaporated
customThe residual oil was purified by silica gel column chromatography (0-50% EtOAc in hexane)

Sources & evidence

ORD record: ord-10f9c9dfa08640e3b6c601685102a34d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829026B2

Reaction notes

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