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Water → 5-(4-Chloro-phenyl)-6-cyclopropylmethoxy-2-trifluoromethyl-nicotinic acid ethyl ester

HRID 1929913
ノート
印刷プレビュー

反応式

HRID 1929913 の反応式
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9](Br)[C:8]([O:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[N:7][C:6]=1[C:17]([F:20])([F:19])[F:18])[CH3:2].[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.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>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9]([C:26]2[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=2)[C:8]([O:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[N:7][C:6]=1[C:17]([F:20])([F:19])[F:18])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 675049975-Bromo-6-cyclopropylmethoxy-2-trifluoromethyl-nicotinic acid ethyl ester

生成物 1

HCID 675046855-(4-Chloro-phenyl)-6-cyclopropylmethoxy-2-trifluoromethyl-nicotinic acid ethyl ester収率 114.3%

試薬・触媒・溶媒 2

HCID 178418807
HCID 178418807、化合物
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

5-Bromo-6-cyclopropylmethoxy-2-trifluoromethyl-nicotinic acid ethyl ester (0.3 g, 0.81 mmol) was dissolved in dioxane (1.6 mL). To this solution was added with stirring [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) CH2Cl2 (33 mg, 0.04 mmol), 4-chlorophenylboronic acid (197 mg, 1.2 mmol) and sodium carbonate solution (2M, 1.2 mL). This mixture was heated to 80° C. for 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 (dichloromethane/methanol, 4:1) to give the title compound (0.37 g) as light yellow oil; MS (ISP) 400.1 (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 (dichloromethane/methanol, 4:1)

出典と根拠

ORDレコード
ord-e9cf95d844e04e0c9c844ac2ad3a30c6
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08188093B2

反応ノート

読み込み中…

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