Ethyl 2-fluoro-4-iodobenzoate → HCID 21846688, 화합물

HRID 619655노트

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HRID 619655 반응식
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[CH2:7][C:6]2=[O:15])#[CH:2].[F:16][C:17]1[CH:27]=[C:26](I)[CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>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>[F:16][C:17]1[CH:27]=[C:26]([C:2]#[C:1][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[O:9][C:8]([CH3:13])([CH3:14])[CH2:7][C:6]3=[O:15])[CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

참가 물질

6

반응물 2

HCID 18761561Ethyl 2-fluoro-4-iodobenzoateHCID 21846681HCID 21846681, 화합물2회

생성물 1

HCID 21846688HCID 21846688, 화합물수율 72.8%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

A solution of 6-ethynyl-2,2-dimethylchroman-4-one (Compound 262, 314.0 mg, 1.57 mmol) and ethyl 2-fluoro-4-iodobenzoate (440.0 mg, 1.50 mmol) in 10.0 mL Et3N was purged with argon for 15 minutes. To this solution was added bis(triphenylphosphine)-palladium(II) chloride (275.0 mg, 0.39 mmol) and copper(I) iodide (75.0 mg, 0.39 mmol). After sparging for an additional 10 minutes with argon, the solution was stirred overnight at room temperature. The reaction mixture was filtered through a pad of Celite using an Et2O wash. Concentration of the filtrate under reduced pressure, followed by column chromatography (3-5% EtOAc-hexanes) of the residual solid afforded 400.0 mg (69%) the title compound as an orange solid. 1H NMR (300 MHz, CDCl3) δ: 8.05 (1H, d, J=2.1 Hz), 7.90 (1H, d, J=7.8 Hz), 7.60 (1H, dd, J=2.2 8.5 Hz), 7.29 (1H, dd, J=1.5, 8.2 Hz), 7.25 (1H, d, J=11.4 Hz), 6.93 (1H, d, J=8.5 Hz), 4.39 (2H, q, J=7.1 Hz), 2.75 (2H, s), 1.48 (6H, s), 1.40 (3H, t, J=7.1 Hz).

후처리

  1. customAfter sparging for an additional 10 minutes with argon
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. washwash

출처 및 근거

ORD 기록
ord-7ed4ff2f9c1e41f4a28c001613e8721c
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05958954

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