Triethylamine → 2-(1-(4-Bromophenyl)-3,3-dimethoxycyclobutyl)isoindoline-1,3-dione

HRID 1509317Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH2:16])[CH2:11][C:10]([O:14][CH3:15])([O:12][CH3:13])[CH2:9]2)=[CH:4][CH:3]=1.[O:17]=[C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])N1C(OCC)=O.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([N:16]3[C:18](=[O:17])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]3=[O:27])[CH2:11][C:10]([O:14][CH3:15])([O:12][CH3:13])[CH2:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-(4-bromophenyl)-3,3-dimethoxycyclobutanamine (0.66 g, 2.306 mmol), ethyl 1,3-dioxoisoindoline-2-carboxylate (0.56 g, 2.55 mmol) and triethylamine (1.3 ml, 9.33 mmol) in CHCl3 (15 ml) was heated at 70° C. for 16 h. The reaction mixture was concentrated to as dry as possible. Methanol (˜5 ml) was added. The solution was concentrated to dryness. Methanol (˜5 ml) was added again and the resulted solid was collected by filtration to afford product as a white solid (0.39 g). 1H NMR (500 MHz, CDCl3): 7.70 (dd, 2H), 7.60 (dd, 2H), 7.44 (dd, 2H), 7.37 (dd, 2H), 3.18 (m, 4H), 3.10 (s, 3H), 3.02 (s, 3H).

Workup

concentrationThe reaction mixture was concentrated
customto as dry as possible
additionMethanol (˜5 ml) was added
concentrationThe solution was concentrated to dryness
additionMethanol (˜5 ml) was added again
filtrationthe resulted solid was collected by filtration

Sources & evidence

ORD record: ord-3abab01d6f2c4f4082bbd3c159f97c4f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

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