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

HRID 592210

반응식

HRID 592210 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c3973b6529bb4741881e2623278479f7
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238646B2

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