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

HRID 1944862노트

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HRID 1944862 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

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온도
110 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-b142cb6eb8514a8ba655f3f9bdac79a3
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394829B2

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