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

HRID 1771602ノート

反応式

HRID 1771602 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-7c4b4b645bda4502a93ffc9a7dcb4b77
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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