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

HRID 1771603노트

반응식

HRID 1771603 반응식
Br[C:2]1[CH:3]=[C:4]([CH2:9][NH:10][C:11]2[C:12]([F:26])=[C:13]([CH:22]=[CH:23][C:24]=2[F:25])[O:14][CH2:15][C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:26][C:12]1[C:11]([NH:10][CH2:9][C:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([F:27])[CH:33]=3)[CH:3]=2)=[C:24]([F:25])[CH:23]=[CH:22][C:13]=1[O:14][CH2:15][C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 89444123Isopropyl 2-[3-[(3-bromo-5-methyl-phenyl)methylamino]-2,4-difluoro-phenoxy]acetate

생성물 1

HCID 89443771Isopropyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]phenoxy]acetate수율 78.9%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6342Acetonitrile용매

실험 절차

To a solution of isopropyl 2-[3-[(3-bromo-5-methyl-phenyl)methylamino]-2,4-difluoro-phenoxy]acetate (176 mg, 0.4 mmol, 1.0 eq) in acetonitrile (15 mL) was added 3-fluorophenylboronic acid (86 mg, 0.61 mmol, 1.5 eq), K2CO3 (142 mg, 1.03 mmol, 2.5 eq) and Pd(dppf)Cl2 (15 mg, 0.02 mmol, 0.05 eq). The mixture was heated at reflux overnight then the solvent was removed in vacuo. The residue was diluted with CH2Cl2, washed with water, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by chromatography (petroleum ether: EtOAc, 150:1 to 60:1) to give the title compound as an oil (140 mg, 77%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customthe solvent was removed in vacuo
  4. additionThe residue was diluted with CH2Cl2
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by chromatography (petroleum ether: EtOAc, 150:1 to 60:1)

출처 및 근거

ORD 기록
ord-2afb127fd68d4453a93ce275a8597b16
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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