Sodium Carbonate → HCID 19921681、化合物

HRID 1647793ノート

反応式

HRID 1647793 の反応式
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1I.[CH3:14][C:15]([Si:18]([CH3:30])([CH3:29])[O:19][CH2:20][CH2:21][CH2:22][C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:17][C:15]([Si:18]([CH3:29])([CH3:30])[O:19][CH2:20][CH2:21][CH2:22][C:23]1[C:3]2[C:2](=[CH:12][CH:11]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=2)[NH:1][C:24]=1[Si:25]([CH3:26])([CH3:27])[CH3:28])([CH3:14])[CH3:16]

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 459320Ethyl 4-amino-3-iodobenzoateHCID 10923628HCID 10923628、化合物

生成物 1

HCID 19921681HCID 19921681、化合物収率 65%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of ethyl 4-amino-3-iodobenzoate {Hirschfeld et al. J. Med Chem. 1992, 35, 2231-2238.}(7.80 g, 26.8 mmol), [5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-pentynyl]trimethylsilane (9.41 g, 34.8 mmol), tetra-n-butylammonium chloride (7.44 g, 26.8 mmol), sodium carbonate (14.20 g, 0.134 mol), triphenylphosphine (0.35 g, 1.3 mmol), and palladium (II) acetate (0.30 g, 1.3 mmol) in 200 mL of DMF, was heated at 98° C. under N2 for 2 h. The solution was cooled, and the bulk of the DMF was removed in vacuo. The mixture was diluted with ethyl acetate, and the organic solution was washed with aqueous NaHCO3, dried (brine, MgSO4), filtered, and concentrated in vacuo. Silica gel chromatography (10:1 hexanes-EtOAc) of the concentrate yielded the title compound (7.49 g, 65%) as a crystalline solid. Recrystallization from hexanes provided an analytical sample as a white crystalline solid: mp 115- 116° C. Anal. Calcd for C23H39N1O3Si2 : C 63.69; H, 9.06; N, 3.23. Found: C, 63.54; H, 9.11; N, 3.17.

後処理

  1. temperatureThe solution was cooled
  2. customthe bulk of the DMF was removed in vacuo
  3. additionThe mixture was diluted with ethyl acetate
  4. washthe organic solution was washed with aqueous NaHCO3
  5. dry with materialdried (brine, MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8942478b94324e07b82c413ce4f54ceb
出典データセット
uspto-grants-1995_07
特許番号
US05434154

反応ノート

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