Potassium Phosphate, Tribasic → 4-Cyclopropyl-N-methylaniline

HRID 63647노트

반응식

HRID 63647 반응식
Br[C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.[CH:10]1(B(O)O)[CH2:12][CH2:11]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:10]1([C:2]2[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=2)[CH2:12][CH2:11]1

참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 2757052Benzenamine, 4-bromo-N-methyl-HCID 2760897Cyclopropylboronic acid

생성물 1

HCID 153651924-Cyclopropyl-N-methylaniline수율 68%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

To a suspension of 4-bromo-N-methylaniline (500 mg, 2.69 mmol), cyclopropylboronic acid (462 mg, 5.38 mmol), (cyclohexyl)3P+HBF4− (99 mg, 0.27 mmol) and K3PO4 (2.0 g, 9.4 mmol) in toluene (20 mL) and H2O (1 mL) was added Pd(OAc)2 (36 mg, 0.16 mmol) at r.t. under N2. The reaction was stirred at reflux overnight. The reaction was filtered, concentrated, and purified by silica gel chromatography (PE:EtOAc=10:1) to give 268 mg (68%) of the title compound as a brown oil. [M+H] Calc'd for C10H23N, 148. Found, 148.

후처리

  1. temperatureat reflux overnight
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (PE:EtOAc=10:1)

출처 및 근거

ORD 기록
ord-a03e03868c984fbcb98c3d1ffc13029b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447046B2

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