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

HRID 2205864ノート

反応式

HRID 2205864 の反応式
[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

参加物

8

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒2 回HCID 8471Triethylamine溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0b67e1aed9f143caa376a7ef6b23a970
出典データセット
uspto-grants-2016_06
特許番号
US09371319B2

反応ノート

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