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

HRID 2046062ノート

反応式

HRID 2046062 の反応式
[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].[CH:19]1[C:24]([I:25])=[CH:23][CH:22]=[C:21](I)[CH:20]=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:21]2[CH:20]=[CH:19][C:24]([I:25])=[CH:23][CH:22]=2)[CH:6]=1)=[O:4]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of product of Step B (0.25 g, 1 mmol), 1,4 di-idobenzene (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).

後処理

  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)

出典と根拠

ORDレコード
ord-3f30043d8f7840adaa6a4e9e6046112c
出典データセット
uspto-grants-2013_11
特許番号
US08592399B2

反応ノート

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