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

HRID 594797ノート

反応式

HRID 594797 の反応式
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

参加物

7

反応物 3

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

生成物 1

HCID 153651924-Cyclopropyl-N-methylaniline収率 68%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-aa045eb2745248ef8d9fb592f067d491
出典データセット
uspto-grants-2016_01
特許番号
US09242968B2

反応ノート

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