Potassium Phosphate, Tribasic → 4-cyclopropyl-3-Methoxyaniline

HRID 471954노트

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HRID 471954 반응식
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].[CH:11]1(B(O)O)[CH2:13][CH2:12]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1.O>[CH:11]1([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:9][CH3:10])[CH2:13][CH2:12]1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 70182544-Bromo-3-methoxyaniline

생성물 1

HCID 593949554-cyclopropyl-3-Methoxyaniline수율 25%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 22272177Toluene water용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 4-bromo-3-methoxyaniline (1 g, 4.98 mmol) in 3:2 toluene/water (10 mL) was added cyclopropylboronic acid (514 mg, 5.98 mmol), Pd(OAc)2 (56 mg, 0.25 mmol), PCy3 (140 mg, 0.5 mmol) and K3PO4 (3.18 g, 15 mmol) at room temperature. The mixture was stirred at 100° C. for 10 h. The solid was filtered and the filtrate concentrated in vacuo. Purification by silica gel chromatography (2-10% ethyl acetate/hexanes) provided 4-cyclopropyl-3-methoxyaniline (200 mg, 25%) as a brown solid. 1H NMR (300 MHz, CDCl3) 6.67 (d, J=7.8 Hz, 1H), 6.24-6.20 (m, 2H), 3.82 (s, 3H), 3.50 (brs, 2H), 2.02-1.95 (m, 1H), 0.85-0.79 (m, 2H), 0.57-0.51 (m, 2H).

후처리

  1. filtrationThe solid was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by silica gel chromatography (2-10% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-929b6441b29943cbab441d7158e13001
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633189B2

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