Triethylamine → Diethyl 2,6-diisopropyl-4-[(2-trimethylsilylethynyl)phenyl]pyridine-3,5-dicarboxylate

HRID 324861

反応式

HRID 324861 の反応式
[CH:1]([C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2I)[C:7]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:6]([CH:27]([CH3:29])[CH3:28])[N:5]=1)([CH3:3])[CH3:2].[CH3:30][Si:31]([C:34]#[CH:35])([CH3:33])[CH3:32].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu](I)I>[CH:1]([C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:35]#[C:34][Si:31]([CH3:33])([CH3:32])[CH3:30])[C:7]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:6]([CH:27]([CH3:29])[CH3:28])[N:5]=1)([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 22005000Diethyl 2,6-diisopropyl-4-(2-iodophenyl)pyridine-3,5-dicarboxylate

生成物 1

HCID 22005127Diethyl 2,6-diisopropyl-4-[(2-trimethylsilylethynyl)phenyl]pyridine-3,5-dicarboxylate収率 83.3%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒

実験手順

A solution of 1.50 g (3 mmole) of the intermediate obtained in Step A in toluene was treated with 1.48 g (15 mmole) of trimethylsilyl acetylene, 87.1 g (0.86 mol) of triethylamine, 0.1 g (0.15 mmol) of bis(triphenylphosphine) palladium(II) chloride, 0.2 g (0.8 mmole) of triphenyl phosphine and 0.2 g (1.17 mmole) of copper iodide. This reaction mixture was stirred at rt for 1 hr and heated at 90° C., in a sealed reaction vessel, for 16 hrs. The reaction mixture was to cooled to temperature, filtered through Celite, and stripped to give a dark oil which upon purification by flash silica gel chromatography to yield 1.22 g (2.5 mmole) of the product. 1H NMR (300 MHz, CDCl3): δ 0.0 (s, 9 H), 0.93 (t, J=7.0, 61), 1.32 (d, J=6.6 Hz, 6 H), 1.33 (d, J=6.6 Hz, 6 H), 3.18 (septet, J=6.6, 2 H), 3.90 (q, J=7.0 Hz, 4 H), 7.20-7.50 (m, 4 H).

後処理

  1. temperatureheated at 90° C., in a sealed reaction vessel, for 16 hrs
  2. temperatureto cooled to temperature
  3. filtrationfiltered through Celite
  4. customto give a dark oil which
  5. customupon purification by flash silica gel chromatography

出典と根拠

ORDレコード
ord-2047284ce66a4eb491d40b169aa2e5d1
出典データセット
uspto-grants-2001_04
特許番号
US06218431B1

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