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

HRID 473518
Notes
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Reaction equation

HRID 473518 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 66827Phenylboronic AcidHCID 672031272-(5-(3-Bromophenyl)pent-4-ynyl)isoindoline-1,3-dione

Product 1

HCID 672024882-(5-(Biphenyl-3-yl)pent-4-ynyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-Dimethoxyethane
Solvent

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

  1. customThe reaction was then quenched with saturated NaHCO3
  2. extractionthe resulting mixture extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed in vacuo
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes