3-Bromo-5-methoxypyridine → 3-(4-Fluoro-3-methylphenylethynyl)-5-methoxypyridine

HRID 606884

反応式

HRID 606884 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([CH3:19])[CH:13]=1)#[CH:11]>C(NC(C)C)(C)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]#[C:11][C:2]2[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=2)=[CH:13][C:14]=1[CH3:19]

参加物

7

反応物 2

HCID 8171633-Bromo-5-methoxypyridineHCID 162137974-Ethynyl-1-fluoro-2-methylbenzene2 回

生成物 1

HCID 670474533-(4-Fluoro-3-methylphenylethynyl)-5-methoxypyridine収率 51.1%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 7912Diisopropylamine溶媒

反応条件

温度
60 °C

実験手順

Dissolve 3-bromo-5-methoxypyridine (1.0 g, 5.35 mmol) in diisopropylamine (17 mL) and toluene (10 mL) under nitrogen. Add tetrakis(triphenylphosphine)palladium (0.200 g, 0.16 mmol). Heat at 60° C. and add 4-ethynyl-1-fluoro-2-methylbenzene (717 mg, 5.35 mmol) and copper (I) iodide (20 mg, 0.11 mmol). After 20 h add additional 4-ethynyl-1-fluoro-2-methylbenzene (100 mg, 0.75 mmol) and heat at 60° C. for 5 h. Concentrate and purify using silica gel chromatography, eluting with 30:70 to 40:60 ethyl acetate:hexanes, to give the title compound (660 mg, 51%).

後処理

  1. temperatureheat at 60° C. for 5 h
  2. concentrationConcentrate
  3. custompurify
  4. washeluting with 30:70 to 40:60 ethyl acetate

出典と根拠

ORDレコード
ord-f3df2be9dc0a47619caf9aebe8412b39
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

関連ノート

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