1-Octyne → 5-(Oct-1-ynyl)-2-tritylisoindoline

HRID 710283Notes

Reaction equation

HRID 710283 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:5]2.[CH:30]#[C:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>CN(C=O)C.[Cu]I>[C:30]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:5]2)#[C:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 2

HCID 123701-OctyneHCID 667262485-Iodo-2-tritylisoindoline

Product 1

HCID 667262275-(Oct-1-ynyl)-2-tritylisoindolineYield 89%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of the product of Step C (0.2 g; 0.41 mmol), 1-octyne (0.091 ml; 0.62 mmol), Cl2Pd(PPh3)2 (0.02 g; 0.028 mmol) and CuI (0.005 g; 0.026 mmol) in anhydrous DMF (2 ml) was degassed under reduced pressure and saturated with dry N2. After addition of DIPEA (0.5 ml), the resulting mixture was stirred overnight at room temperature under N2. The solvents were removed in vacuo and the residue was diluted to 15 ml with EtOAc and washed with 5% citric acid, 5% NaHCO3, H2O, brine and dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by FCC (SiO2; hexane/EtOAc; 9:1) to give the title compound (0.17 g; 89%) as a colourless syrup. 1H-NMR (CDCl3) 0.93 (m, 3H); 1.34-1.64 (m, 8H); 2.4 (tr, 2H, J=7.1 Hz); 3.94 (s, 4H); 7.0-7.64 (m, 18H).

Workup

  1. customwas degassed under reduced pressure and saturated with dry N2
  2. additionAfter addition of DIPEA (0.5 ml)
  3. customThe solvents were removed in vacuo
  4. additionthe residue was diluted to 15 ml with EtOAc
  5. washwashed with 5% citric acid, 5% NaHCO3, H2O, brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness under reduced pressure
  9. customthe residue was purified by FCC (SiO2; hexane/EtOAc; 9:1)

Sources & evidence

ORD record
ord-927d2a5d3eac469b98766d946bf5847e
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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