Ethyl 4-iodobenzoate → HCID 21846648, compound

HRID 619614Notes

Reaction equation

HRID 619614 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[S:9][C:8]([CH3:16])([CH3:15])[CH2:7][C:6]2=[O:17])#[CH:2].I[C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1>CCN(CC)CC.C1COCC1.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>[CH3:16][C:8]1([CH3:15])[CH2:7][C:6](=[O:17])[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([C:1]#[C:2][C:19]3[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=3)[CH:4]=2)[S:9]1

Participants

7

Reactant 2

HCID 142891Ethyl 4-iodobenzoateHCID 21846658HCID 21846658, compound2×

Product 1

HCID 21846648HCID 21846648, compoundYield 92.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 6-ethynyl-7-methoxy-2,2-dimethylthiochroman-4-one (Compound 208, 217.0 mg, 0.88 mmol) and ethyl 4-iodobenzoate (245.0 mg, 0.89 mmol) in 10.0 mL Et3N and 2 mL THF was purged with argon for 15 minutes. To this solution was added bis(triphenylphosphine)-palladium(II) chloride (154.0 mg, 0.22 mmol) and copper(I) iodide (42.0 mg, 0.22 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 (5 to 10% EtOAc/hexanes) of the residual solid afforded 320.0 mg (92%) of the title compound as an orange solid. 1H NMR (300 MHz, CDCQ3)δ: 8.29 (1H, s), 8.03 (2H, d, J=8.4 Hz), 7.60 (2H, d, J=8.4 Hz), 6.70 (1H, s), 4.40 (2H, q, J=7.1 Hz), 3.96 (3H, s), 2.86 (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-2206b436d0ae48bbb2e3680f1ccb3f94
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

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