Triethylamine → Ethyl 5-((trimethylsilyl)ethynyl)nicotinate

HRID 606798ノート

反応式

HRID 606798 の反応式
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[C:9](Br)[CH:8]=[N:7][CH:6]=1)[CH3:2].C(N(CC)CC)C.[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22]>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[C:9]([C:25]#[C:24][Si:21]([CH3:23])([CH3:22])[CH3:20])[CH:8]=[N:7][CH:6]=1)[CH3:2]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 140785Ethyl 5-bromopyridine-3-carboxylate

生成物 1

HCID 67047749Ethyl 5-((trimethylsilyl)ethynyl)nicotinate収率 86%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178419050HCID 178419050、化合物触媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of ethyl-5-bromonicotinate (30 g, 130.40 mmol), triethylamine (78 mL) and ethyl acetate (130 mL) is degassed for 15 min. Add trimethylsilylacetylene (88.46 mL, 625.92 mmol), bis(triphenylphosphine)palladium (II) dichloride (4.57 g, 6.52 mmol) and copper (I) iodide (0.25 g, 1.30 mmol) and stir at 50° C. under-nitrogen for 16 h. Cool to room temperature, filter through diatomaceous earth, wash with ethyl acetate, and concentrate. Purify the residue by silica gel chromatography, eluting with 10:1 hexanes:ethyl acetate, to give the title compound (27.7 g, 86%).

後処理

  1. filtrationfilter through diatomaceous earth
  2. washwash with ethyl acetate
  3. concentrationconcentrate
  4. customPurify the residue by silica gel chromatography
  5. washeluting with 10:1 hexanes

出典と根拠

ORDレコード
ord-6b54da0751cb4c979b9b53d0c5f2c2c5
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

反応ノート

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