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

HRID 1771603ノート

反応式

HRID 1771603 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

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

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-2afb127fd68d4453a93ce275a8597b16
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

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