Ethyl 2-fluoro-4-iodobenzoate → HCID 21846688、化合物

HRID 619655ノート

反応式

HRID 619655 の反応式
[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]

参加物

6

反応物 2

HCID 18761561Ethyl 2-fluoro-4-iodobenzoateHCID 21846681HCID 21846681、化合物2 回

生成物 1

HCID 21846688HCID 21846688、化合物収率 72.8%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7ed4ff2f9c1e41f4a28c001613e8721c
出典データセット
uspto-grants-1999_09
特許番号
US05958954

反応ノート

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