Toluene → 2-Fluoro-5-methyl-4-(2-methylpyridin-4-yl)aniline

HRID 1036255

反応式

HRID 1036255 の反応式
Br[C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.[CH3:11][C:12]1[CH:17]=[C:16](B(O)O)[CH:15]=[CH:14][N:13]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C(O)C>[F:10][C:4]1[CH:3]=[C:2]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]([CH3:11])[CH:17]=2)[C:8]([CH3:9])=[CH:7][C:5]=1[NH2:6]

参加物

7

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 41926642-Methylpyridine-4-boronic acidHCID 70180404-Bromo-2-fluoro-5-methylaniline

生成物 1

HCID 584477092-Fluoro-5-methyl-4-(2-methylpyridin-4-yl)aniline

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒

実験手順

To a round bottom flask charged with 4-bromo-2-fluoro-5-methylaniline 191-1 (2.04 g, 10 mmol), 2-methylpyridin-4-ylboronic acid 191-2 (1.37 g, 10 mmol) and Pd(PPh3)4 (0.4 g, 0.35 mmol) was added toluene (30 mL), ethanol (10 mL) and saturated sodium carbonate (10 mL). The flask was flushed with nitrogen and the reaction was heated to reflux for 10 hours. After the reaction was cooled down to room temperature, it was partitioned between ethyl acetate and saturated NaHCO3 and the organic phase was washed with brine and dried over Na2SO4. The solvent was removed by rotary evaporation and the residue was purified by silica gel flash chromatography, eluted with 50% ethyl acetate in hexane to give 2-fluoro-5-methyl-4-(2-methylpyridin-4-yl)aniline 191-3. MS m/z 217.1 (M+1).

後処理

  1. customThe flask was flushed with nitrogen
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 10 hours
  4. customit was partitioned between ethyl acetate and saturated NaHCO3
  5. washthe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed by rotary evaporation
  8. customthe residue was purified by silica gel flash chromatography
  9. washeluted with 50% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-96958b7b2d6d4870a5bb76f8d677fabf
出典データセット
uspto-grants-2013_10
特許番号
US08546396B2

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