Triethylamine → 5-(3,4-Dimethylphenylethynyl)-nicotinonitrile

HRID 606838

反応式

HRID 606838 の反応式
I[C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([CH3:8])=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:17]([C:19]1[CH:20]=[N:21][CH:22]=[C:23]([CH:26]=1)[C:24]#[N:25])#[CH:18]>C(#N)C.C(OCC)C.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>[CH3:9][C:4]1[CH:3]=[C:2]([C:18]#[C:17][C:19]2[CH:20]=[N:21][CH:22]=[C:23]([CH:26]=2)[C:24]#[N:25])[CH:7]=[CH:6][C:5]=1[CH3:8]

参加物

8

反応物 3

HCID 8471TriethylamineHCID 1416464-Iodo-1,2-dimethylbenzeneHCID 224165635-Ethynylnicotinonitrile

生成物 1

HCID 670475425-(3,4-Dimethylphenylethynyl)-nicotinonitrile収率 62%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178419050HCID 178419050、化合物触媒HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

実験手順

Combine 4-iodo-o-xylene (0.362 g, 1.561 mmol), bis(triphenylphosphine)palladium (II) dichloride (55 mg, 0.078 mmol), and copper (I) iodide (30 mg, 0.156 mmol) in triethylamine (0.653 mL, 4.683 mmol) and stir under nitrogen for 5 min at 80° C. Add a solution of 5-ethynylnicotinonitrile, (prepared essentially as described in PREPARATION 4), (200 mg, 1.561 mmol) in anhydrous acetonitrile (2.50 mL), and stir under nitrogen overnight. Cool to room temperature and dilute with diethyl ether. Wash with a saturated aqueous solution of sodium bicarbonate, dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with 95:5 to 50:50 dichloromethane:ethyl acetate, to give the title compound as a yellow solid (225 mg, 62%).

後処理

  1. custom(prepared essentially
  2. washWash with a saturated aqueous solution of sodium bicarbonate
  3. dry with materialdry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with 95:5 to 50:50 dichloromethane

出典と根拠

ORDレコード
ord-f070616815b445c8816ea82e3b9c3f6a
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

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