p-Diiodobenzene → 2,2,2-Trifluoro-1-(1-(3-(4-iodophenyl)prop-2-ynyl)-1H-indol-3-yl)ethanone

HRID 717645Notes

Reaction equation

HRID 717645 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][C:15]#[CH:16])[CH:6]=1)=[O:4].[I:19][C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=1>CN(C=O)C.[Cu]I>[F:18][C:2]([F:1])([F:17])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][C:15]#[C:16][C:23]2[CH:24]=[CH:25][C:20]([I:19])=[CH:21][CH:22]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 12208p-DiiodobenzeneHCID 866617692,2,2-Trifluoro-1-(1-(prop-2-ynyl)-1H-indol-3-yl)ethanone

Product 1

HCID 667264982,2,2-Trifluoro-1-(1-(3-(4-iodophenyl)prop-2-ynyl)-1H-indol-3-yl)ethanoneYield 61.8%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of product of Step B (0.25 g, 1 mmol), 1,4 di-iodobenzene (0.4 g, 1.2 mmol) Cl2Pd(PPh3)2 (0.06 g) and catalytic amount of CuI in a mixture of DMF:DIPEA (10 ml: 0.5 ml) at room temperature was degassed under reduced pressure and saturated with N2. This was stirred overnight at room temperature, quenched with NaHCO3 solution and diluted to 50 ml with EtOAc. The organic layer was separated and washed with H2O, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2, hexane/EtOAc) to give the title compound (0.28 g, 51%), as light yellow solid. 1H-NMR (CDCl3) 8.43-8.40 (b, 1H); 8.12 (b, 1H); 7.66 (t, 2H, J=8.36 Hz); 7.55-7.51 (m, 1H); 7.44-7.38 (m, 2H); 7.14 (d, 2H, J=8.30 Hz); 5.16 (s, 2H).

Workup

  1. customDIPEA (10 ml: 0.5 ml) at room temperature was degassed under reduced pressure and saturated with N2
  2. customquenched with NaHCO3 solution
  3. additiondiluted to 50 ml with EtOAc
  4. customThe organic layer was separated
  5. washwashed with H2O
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by FCC (SiO2, hexane/EtOAc)

Sources & evidence

ORD record
ord-b6b0ef93a31048b280fdef846507e35f
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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