4-Ethynyl-1-methyl-1H-pyrazole → 2-bromo-5-((1-methyl-1H-pyrazol-4-yl)ethynyl)pyridin-4-amine

HRID 2205864노트

반응식

HRID 2205864 반응식
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5](I)=[CH:4][N:3]=1.[C:10]([C:12]1[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=1)#[CH:11]>CN(C=O)C.C(N(CC)CC)C.C(OCC)(=O)C.[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:7]=[C:6]([NH2:8])[C:5]([C:11]#[C:10][C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[CH:4][N:3]=1

참가 물질

8

반응물 2

HCID 511383214-Ethynyl-1-methyl-1H-pyrazoleHCID 601457042-Bromo-5-iodopyridin-4-amine

생성물 1

HCID 867062772-bromo-5-((1-methyl-1H-pyrazol-4-yl)ethynyl)pyridin-4-amine수율 88.2%

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매2회HCID 8471Triethylamine용매2회HCID 8857Ethyl Acetate용매

실험 절차

4-Amino-2-bromo-5-iodopyridine (5) (2.58 g 8.63 mmole), copper(I) iodide (164 mg 0.86 mmole) and bis(triphenylphosphine)palladium dichloride (216 mg 0.432 mmole) were weighed into a 100 mL flask and DMF (25 mL) with triethylamine (22 mL) was added. The mixture was stirred at r.t. for 15 minutes under nitrogen. 4-Ethynyl-1-methyl-1H-pyrazole (20) (945 mg at 100%, 8.91 mmole) in DMF (10 mL) and triethylamine (5 mL) was added to the flask. The reaction was stirred at r.t. for 1.75 hrs. The reaction was diluted with ethyl acetate (450 mL) and the solution was washed with water (3×240 mL), brine (120 mL), dried and evaporated. The residue was flash chromatographed (silica/ethyl acetate) to give the title compound (2.11 g, 88%). 1H-NMR (CDCl3, 500 MHz): δ 3.94 (s, 3H), 4.80 (br s, 2H), 6.79 (s, 1H), 7.59 (s, 1H), 7.66 (s, 1H), 8.15 (s, 1H).

후처리

  1. stirringThe reaction was stirred at r.t. for 1.75 hrs
  2. washthe solution was washed with water (3×240 mL), brine (120 mL)
  3. customdried
  4. customevaporated
  5. customchromatographed (silica/ethyl acetate)

출처 및 근거

ORD 기록
ord-0b67e1aed9f143caa376a7ef6b23a970
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371319B2

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