4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → Methyl 4-(4'-amino-[1,1'-biphenyl]-4-yl)butanoate

HRID 1944862ノート

反応式

HRID 1944862 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)O1.I[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:20][CH:19]=1.C(Cl)Cl.CO>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:13][C:12]1[CH:11]=[CH:10][C:9]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 11403935Methyl 4-(4-iodophenyl)butanoateHCID 21226129Dichloromethane methanol

生成物 1

HCID 57516934Methyl 4-(4'-amino-[1,1'-biphenyl]-4-yl)butanoate収率 82.5%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
110 °C

実験手順

Solid 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (158 mg, 0.723 mmol) and Pd(PPh3)4 (38 mg, 0.033 mmol) were added to a solution of methyl 4-(4-iodophenyl)butanoate (200 mg, 0.657 mmol) in dimethoxyethane/2M Na2CO3 (3 mL, 2:1) at rt. The resulting mixture was degassed with argon gas then heated at 110° C. using microwave for 30 min. The reaction mixture was diluted with EtOAc (10 mL) then washed with H2O (10 mL), brine (10 mL), dried over Na2SO4, and concentrated to give crude (294 mg) as brown oil. Chromatography (9:1, CH2Cl2/MeOH) afforded the title compound (146 mg, 82%) as a light yellow solid. ES/MS calcd. for C17H20NO2+ 270.2. Found m/z=270.2 (M+H)+.

後処理

  1. customThe resulting mixture was degassed with argon gas
  2. customfor 30 min
  3. additionThe reaction mixture was diluted with EtOAc (10 mL)
  4. washthen washed with H2O (10 mL), brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give crude (294 mg) as brown oil

出典と根拠

ORDレコード
ord-b142cb6eb8514a8ba655f3f9bdac79a3
出典データセット
uspto-grants-2013_03
特許番号
US08394829B2

反応ノート

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