Sodium Carbonate → 2-(2-Fluoro-5-methylphenyl)pyridin-4-amine

HRID 1522555노트

반응식

HRID 1522555 반응식
Br[C:2]1[CH:7]=[C:6]([NH:8]C(=O)OC(C)(C)C)[CH:5]=[CH:4][N:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 70155224-(Boc-amino)-2-bromopyridineHCID 103518842-Fluoro-5-methylbenzeneboronic acid

생성물 1

HCID 674695782-(2-Fluoro-5-methylphenyl)pyridin-4-amine수율 532.9%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

Bis(triphenylphosphine)palladium chloride (0.406 g, 0.578 mmol), tert-butyl 2-bromopyridin-4-ylcarbamate (250 mg, 0.915 mmol), and 2-fluoro-5-methylphenylboronic acid (1.157 g, 7.51 mmol) and sodium carbonate (0.458 ml, 0.915 mmol) were combined in dioxane (10 mL) and heated to reflux for 5 hours. The reaction mixture was cooled, evaporated to remove most of the solvent, and partitioned between brine and EtOAc. The organic layer was separated and dried over Na2SO4, filtered, and concentrate under vacuum to give a residue which was purified by NH silica column chromatography eluting with Hex/EtOAc 1:1 to give a residue which was further purified by repeating the silica column chromatography using the same conditions to give the title compound (986 mg) as clear oil which solidified on standing. ESI-MS: m/z 203.1 (M+H).

후처리

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. temperatureThe reaction mixture was cooled
  4. customevaporated
  5. customto remove most of the solvent
  6. custompartitioned between brine and EtOAc
  7. customThe organic layer was separated
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrate under vacuum
  11. customto give a residue which
  12. customwas purified by NH silica column chromatography
  13. washeluting with Hex/EtOAc 1:1
  14. customto give a residue which
  15. customwas further purified

출처 및 근거

ORD 기록
ord-eb2fdcfdfc37494581094e76156dd105
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073918B2

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