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

HRID 471954ノート

反応式

HRID 471954 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 593949554-cyclopropyl-3-Methoxyaniline収率 25%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 22272177Toluene water溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-929b6441b29943cbab441d7158e13001
出典データセット
uspto-grants-2014_01
特許番号
US08633189B2

反応ノート

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