Ethyl 4-iodobenzoate → HCID 67553060, compound

HRID 619613Notes

Reaction equation

HRID 619613 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[F:13])[S:9][C:8]([CH3:15])([CH3:14])[CH2:7][C:6]2=[O:16])#[CH:2].I[C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1>CCN(CC)CC.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>[CH3:15][C:8]1([CH3:14])[CH2:7][C:6](=[O:16])[C:5]2[C:10](=[CH:11][C:12]([F:13])=[C:3]([CH2:1][CH2:2][C:18]3[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=3)[CH:4]=2)[S:9]1

Participants

6

Reactant 2

HCID 142891Ethyl 4-iodobenzoateHCID 21846674HCID 21846674, compound2×

Product 1

HCID 67553060HCID 67553060, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 6-ethynyl-7-fluoro-2,2-dimethylthiochroman-4-one (Compound 207, 330.0 mg, 1.41 mmol) and ethyl 4-iodobenzoate (392 mg, 1.41 mmol) in 10.0 mL Et3N was purged with argon for 15 minutes. To this solution was added bis(triphenylphosphine)-palladium(II) chloride (247 mg, 0.35 mmol) and copper(I) iodide (67.0 mg, 0.35 mmol). After sparging for an additional 10 minutes with argon, the solution was stirred overnight at room temperature. The reaction mixture was diluted with EtOAc and filtered through a pad of Celite using an EtOAc wash. Concentration of the filtrate under reduced pressure, followed by column chromatography (3 to 5% EtOAc/hexanes) of the residual solid afforded 490.0 mg (91%) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3)δ: 8.31 (1H, d, J=7.6 Hz), 8.04 (2H, d, J=8.3 Hz), 7.60 (2H, d, J=8.3 Hz), 7.00 (1H, d, J=9.3 Hz), 4.40 (2H, q, J=7.1 Hz), 2.89 (2H, s), 1.50 (6H, s), 1.41 (3H, t, J=7.1 Hz).

Workup

  1. customAfter sparging for an additional 10 minutes with argon
  2. additionThe reaction mixture was diluted with EtOAc
  3. filtrationfiltered through a pad of Celite
  4. washwash

Sources & evidence

ORD record
ord-afb6eb48aaf544a18a4e17505395346a
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

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