Potassium Phosphate, Tribasic → (4-Amino-3-methoxyphenyl)diethylphosphine oxide

HRID 921474ノート

反応式

HRID 921474 の反応式
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1.[CH2:11]([PH:13](=[O:16])[CH2:14][CH3:15])[CH3:12].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:11]([P:13]([C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1)([CH2:14][CH3:15])=[O:16])[CH3:12]

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 4592574-Bromo-2-methoxyanilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178477251HCID 178477251、化合物

生成物 1

HCID 67052703(4-Amino-3-methoxyphenyl)diethylphosphine oxide

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-bromo-2-methoxyaniline (0.100 g, 0.495 mmol) in 2 mL DMF was added diethylphosphine oxide (0.0730 g, 0.544 mmol), palladium acetate (5.6 mg, 0.025 mmol), XANTPHOS (17.2 mg, 0.030 mmol), and potassium phosphate (0.116 g, 0.544 mmol). The mixture was purged with nitrogen, and subjected to microwaves at 150° C. for 20 minutes. The reaction mixture was concentrated and purified by silica gel chromatography (0-12% 7N ammonia in methanol:dichloromethane) and the fractions were concentrated. The residue was acidified with 2.5 M HCl in ethanol and the solution was concentrated to provide 4-(diethylphosphoryl)-2-methoxyaniline as the hydrochloride salt (0.132 g, 91% yield).

後処理

  1. customThe mixture was purged with nitrogen
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by silica gel chromatography (0-12% 7N ammonia in methanol:dichloromethane)
  4. concentrationthe fractions were concentrated
  5. concentrationthe solution was concentrated

出典と根拠

ORDレコード
ord-837be26b917b4e1499cfcdab7e2e6b65
出典データセット
uspto-grants-2016_03
特許番号
US09273077B2

反応ノート

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