Water → 5-(4-Chloro-phenyl)-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester

HRID 1929802ノート

反応式

HRID 1929802 の反応式
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](Br)[C:7]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:6][CH:5]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.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].C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)[C:7]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:6][CH:5]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 675049645-Bromo-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester

生成物 1

HCID 675049675-(4-Chloro-phenyl)-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester収率 56.8%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

5-Bromo-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester (8.7 g, 29 mmol) was dissolved in toluene (85 mL). To this solution was added with stirring [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) CH2Cl2 (1.2 g, 1.4 mmol), 4-chlorophenylboronic acid (4.9 g, 29 mmol) and sodium carbonate solution (2M, 30 mL). This mixture was heated to 90° C. for 1.5 h and cooled to room temperature. Water (150 mL) was added, the phases were separated and the water mixture was extracted with ethylacetate. Organic phases were pooled, dried with MgSO4 and the volatiles removed in vacuo. The residue was purified by flash chromatography on silica (heptane/ethylacetate, 1:3) to give the title compound (5.3 g) as a pinkish solid; MS (ISP) 322.1 (M+H)+.

後処理

  1. temperaturecooled to room temperature
  2. customthe phases were separated
  3. extractionthe water mixture was extracted with ethylacetate
  4. dry with materialdried with MgSO4
  5. customthe volatiles removed in vacuo
  6. customThe residue was purified by flash chromatography on silica (heptane/ethylacetate, 1:3)

出典と根拠

ORDレコード
ord-a77265ccec1c40ac81b74ad13c40d9da
出典データセット
uspto-grants-2012_05
特許番号
US08188093B2

反応ノート

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