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Sodium Carbonate → N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)-2,3-dimethyl-benzamide

HRID 1771703
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HRID 1771703 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH3:18])[C:11]([CH3:17])=[C:12]([CH:16]=2)[C:13]([OH:15])=O)[CH:5]=[CH:6][CH:7]=1.C(Cl)(C(Cl)=O)=O.[NH2:25][C:26]1[C:27]([F:34])=[C:28]([OH:33])[CH:29]=[CH:30][C:31]=1[F:32].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.C1COCC1.CCOC(C)=O.O.CN(C=O)C>[F:34][C:27]1[C:28]([OH:33])=[CH:29][CH:30]=[C:31]([F:32])[C:26]=1[NH:25][C:13](=[O:15])[C:12]1[CH:16]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH:9]=[C:10]([CH3:18])[C:11]=1[CH3:17]
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참가 물질

10

반응물 4

HCID 10340Sodium CarbonateHCID 65578Oxalyl chlorideHCID 227559833-Amino-2,4-difluorophenolHCID 894435205-(3-Fluorophenyl)-2,3-dimethyl-benzoic acid

생성물 1

HCID 89443837N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)-2,3-dimethyl-benzamide수율 15.7%

시약·촉매·용매 5

HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 6344Dichloromethane용매
HCID 8028Tetrahydrofuran용매2회
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-(3-fluorophenyl)-2,3-dimethyl-benzoic acid (3.82 g, 15.6 mmol, 5.8 eq) in DCM (30 mL) was added (COCl)2 (5.96 g, 46.8 mmol, 17.0 eq) and DMF (0.5 mL). The mixture was stirred at room temperature under N2 for 2 h then the solvent removed in vacuo. The residue obtained was dissolved in THF (10 mL) and added to a mixture of 3-amino-2,4-difluoro-phenol (intermediate X(a)) (0.4 g, 2.75 mmol, 1.0 eq) and Na2CO3 (0.87 g, 8.26 mmol, 3.0 eq) in THF. The reaction was stirred at room temperature overnight then water and EtOAc were added. The organic extract was washed with water, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (DCM:MeOH, 0:1 to 1:50) to give the title compound as a solid (0.16 g, 15%).

후처리

  1. customthe solvent removed in vacuo
  2. customThe residue obtained
  3. stirringThe reaction was stirred at room temperature overnight
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue obtained
  10. customwas purified by column chromatography (DCM:MeOH, 0:1 to 1:50)

출처 및 근거

ORD 기록
ord-a528e0cb9a0944e5babf0e96d91e3ea1
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249085B2

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