Potassium Carbonate → Isopropyl 2-[3-[(3-bromo-5-methyl-phenyl)methylamino]-2,4-difluoro-phenoxy]acetate

HRID 1771602노트

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HRID 1771602 반응식
[NH2:1][C:2]1[C:3]([F:17])=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[O:5][CH2:6][C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8].[Br:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26]Br)[CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O>[Br:18][C:19]1[CH:20]=[C:21]([CH2:26][NH:1][C:2]2[C:3]([F:17])=[C:4]([CH:13]=[CH:14][C:15]=2[F:16])[O:5][CH2:6][C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])[CH:22]=[C:23]([CH3:25])[CH:24]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzeneHCID 89444213Isopropyl 2-(3-amino-2,4-difluoro-phenoxy)acetate

생성물 1

HCID 89444123Isopropyl 2-[3-[(3-bromo-5-methyl-phenyl)methylamino]-2,4-difluoro-phenoxy]acetate수율 31.4%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
100 °C

실험 절차

To a solution of isopropyl 2-(3-amino-2,4-difluoro-phenoxy)acetate (intermediate IV(b)) (350 mg, 1.43 mmol, 1.0 eq) and 1-bromo-3-(bromomethyl)-5-methyl-benzene (528 mg, 1.99 mmol, 1.4 eq) in DMSO (15 mL) was added K2CO3 (593 mg, 4.29 mmol, 3.0 eq). The reaction was heated at 100° C. for 1 h in a microwave reactor, then diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by chromatography (petroleum ether: EtOAc, 100:1 to 80:1) to give the title compound as a light yellow oil (192 mg, 16%).

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography (petroleum ether: EtOAc, 100:1 to 80:1)

출처 및 근거

ORD 기록
ord-7c4b4b645bda4502a93ffc9a7dcb4b77
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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