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

HRID 606838

반응식

HRID 606838 반응식
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]

참가 물질

8

반응물 3

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

생성물 1

HCID 670475425-(3,4-Dimethylphenylethynyl)-nicotinonitrile수율 62%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178419050HCID 178419050, 화합물촉매HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f070616815b445c8816ea82e3b9c3f6a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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