Triethylamine → 2-(5-(3-Bromophenyl)pent-4-ynyl)isoindoline-1,3-dione

HRID 473517Notes

Reaction equation

HRID 473517 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[CH:3]=1.[CH2:9]([N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24])[CH2:10][CH2:11][C:12]#[CH:13].C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:13]#[C:12][CH2:11][CH2:10][CH2:9][N:14]2[C:15](=[O:24])[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]2=[O:23])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 140821-Bromo-3-fluorobenzeneHCID 11769822N-(4-Pentynyl)phthalimide

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

1-Bromo-3-fluoro-benzene (1.0 mL, 7.8 mmol), 2-pent-4-ynyl-isoindole-1,3-dione (1.8 g, 8.6 mmol), Pd(PPh3)2Cl2 (191 mg, 0.27 mmol), CuI (118 mg, 0.62 mmol), and triethylamine (4.4 mL, 31.3 mmol) were taken up into DMF (10 mL) and stirred at room temperature for four hours. The reaction was then quenched with saturated NaHCO3 and the resulting mixture extracted with EtOAc and 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-(3-bromophenyl)pent-4-ynyl)isoindoline-1,3-dione. MH+ 368, 370

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-e7447d44287547cbbed70defc7eb2690
Source dataset
uspto-grants-2014_01
Patent number
US08633322B2

Reaction notes

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