Potassium Carbonate → 3-(4',5'-Difluoro-2'-methoxybiphenyl-4-yloxymethyl)-4-fluorobenzoic acid methyl ester

HRID 1665241ノート

反応式

HRID 1665241 の反応式
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=2)[CH:5]=1.[F:21][C:22]1[C:27]([F:28])=[CH:26][C:25](B(O)O)=[C:24]([O:32][CH3:33])[CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.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]>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:25]3[CH:26]=[C:27]([F:28])[C:22]([F:21])=[CH:23][C:24]=3[O:32][CH3:33])=[CH:15][CH:14]=2)[CH:5]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 16217679(4,5-Difluoro-2-methoxyphenyl)boronic acidHCID 671503534-Fluoro-3-(4-iodophenoxy)methylbenzoic acid methyl ester

生成物 1

HCID 671503573-(4',5'-Difluoro-2'-methoxybiphenyl-4-yloxymethyl)-4-fluorobenzoic acid methyl ester収率 67%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
45 °C

実験手順

To a mixture of 4-fluoro-3-(4-iodophenoxy)methylbenzoic acid methyl ester (1.1 g, 2.85 mmol) and 4,5-difluoro-2-methoxyphenylboronic acid (0.642 g, 3.4 mmol) in DMF (15 mL) and water (2.5 mL) was added Pd(dppf)Cl2 (220 mg, 0.27 mmol) and potassium carbonate (1.24 g, 9.0 mmol). The mixture was stirred at 45° C. overnight and solvents were evaporated. The residue was extracted with ethyl acetate and water. The organic layer was dried and concentrated. The residue was purified through flash column chromatography (120 g silica gel, 5% to 40% ethyl acetate in hexanes over 25 minutes) to give a white solid as 3-(4′,5′-difluoro-2′-methoxybiphenyl-4-yloxymethyl)-4-fluorobenzoic acid methyl ester (0.76 g, 67%).

後処理

  1. customsolvents were evaporated
  2. extractionThe residue was extracted with ethyl acetate and water
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified through flash column chromatography (120 g silica gel, 5% to 40% ethyl acetate in hexanes over 25 minutes)

出典と根拠

ORDレコード
ord-63e2b9ac7335416a8d92a5de3f607588
出典データセット
uspto-grants-2011_10
特許番号
US08039495B2

反応ノート

読み込み中…