Phenylboronic Acid → 2-(5-(Biphenyl-3-yl)pent-4-ynyl)isoindoline-1,3-dione

HRID 473518Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])[CH:5]=[CH:6][CH:7]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[C:2]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-(5-(3-Bromophenyl)pent-4-ynyl)isoindoline-1,3-dione (0.31 g, 0.84 mmol), phenyl boronic acid (206 mg, 1.68 mmol), and Pd (PPh3)4 (0.23, 0.2 mmol) were taken into DME (5 mL) and stirred at 80° C. for two hours. The reaction was then quenched with saturated NaHCO3 and the resulting mixture extracted with EtOAc, washed with brine, then dried over sodium sulfate and the solvent removed in vacuo. The resulting residue was purified on normal phase chromatography (Heptane/EtOAc) to yield 2-(5-(biphenyl-3-yl)pent-4-ynyl)isoindoline-1,3-dione. MH+ 366.3

Workup

customThe reaction was then quenched with saturated NaHCO3
extractionthe resulting mixture extracted with EtOAc
washwashed with brine
dry with materialdried over sodium sulfate
customthe solvent removed in vacuo
customThe resulting residue was purified on normal phase chromatography (Heptane/EtOAc)

Sources & evidence

ORD record: ord-31c8c68df63946318ed47b271f9e3d1e
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633322B2

Reaction notes

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