2-Chloro-4-fluoropyridine → HCID 118223438, 화합물

HRID 2200115노트

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HRID 2200115 반응식
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].CC([O-])(C)C.[K+].[Cl:23][C:24]1[CH:29]=[C:28](F)[CH:27]=[CH:26][N:25]=1>CN1CCCC1=O>[Cl:23][C:24]1[CH:29]=[C:28]([O:8][C:6]2[CH:5]=[CH:4][C:3]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[C:2]([F:1])[CH:7]=2)[CH:27]=[CH:26][N:25]=1

참가 물질

5

반응물 3

HCID 27827922-Chloro-4-fluoropyridineHCID 23665647Potassium tert-butoxideHCID 441857034-(Boc-amino)-3-fluoro-phenol

생성물 1

HCID 118223438HCID 118223438, 화합물수율 79.5%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
0 °C

실험 절차

Dissolve tert-butyl N-(2-fluoro-4-hydroxy-phenyl)carbamate (10.47 g, 46.1 mmol) in N-methyl-2-pyrrolidone (NMP, 100 mL), add t-BuOK (5.67 g, 50.5 mmol) and stir at 0° C. for 30 min. Add 2-chloro-4-fluoropyridine (5.5 g, 41.9 mmol), then stir at 70° C. under N2 for 12 hrs. Quench the reaction with water, extract with EtOAc (300 mL×3), combine the organic layers, wash with brine (300 mL×2), dry over anhydrous Na2SO4. Concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:4) affords the title compound (11.23 g, 79.5%). MS: (M+1): 339.

후처리

  1. customQuench
  2. customthe reaction with water
  3. extractionextract with EtOAc (300 mL×3)
  4. washwash with brine (300 mL×2)
  5. dry with materialdry over anhydrous Na2SO4
  6. concentrationConcentrate under reduced pressure
  7. customto give the crude product
  8. customPurification by chromatography (silica gel, EtOAc:PE=1:4)

출처 및 근거

ORD 기록
ord-c8881961704c4ec3828ecfd84630b876
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359338B2

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