Tetrahydrofuran → 5-Bromo-6-(2-phenylethynyl)pyridin-2-amine

HRID 535382노트

반응식

HRID 535382 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[N:6][C:7]=1Br.[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[CH:11].C(N(CC)CC)C.C1COCC1>C(#N)C.O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[N:6][C:7]=1[C:11]#[C:10][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

9

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 136927815,6-Dibromopyridin-2-amine

생성물 1

HCID 866943675-Bromo-6-(2-phenylethynyl)pyridin-2-amine

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 5,6-dibromopyridin-2-amine (80 g, 318 mmol), ethynylbenzene (78 ml, 698 mmol), copper(I) iodide (1.51 g, 7.94 mmol), Dichlorobis(triphenylphosphine)-palladium(II) (5.79 g, 7.94 mmol) and triethylamine (110 ml, 794 mmol) is stirred under argon atmosphere in ACN (500 ml) with THF (250 ml) for 21 h at 50° C. The mixture is diluted with water and extracted with DCM. The combined organic layers are dried over MgSO4, concentrated in vacuo and the product purified by NP chromatography. Yield: 82 g (94%). HPLC-MS: M+H=273/275; tR=1.34 min (*Method—1).

후처리

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customthe product purified by NP chromatography

출처 및 근거

ORD 기록
ord-78e017eace924fb999574e5f0b82d9bc
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859541B2

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