2-Bromo-5-(trifluoromethyl)benzenamine → 2-(3-Dimethylamino-1-propynyl)-5-(trifluoromethyl)aniline

HRID 502762

反応式

HRID 502762 の反応式
Br[C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1[NH2:4].[CH3:13][N:14]([CH3:18])[CH2:15][C:16]#[CH:17].C(N(C(C)C)CC)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C(#N)C>[CH3:13][N:14]([CH3:18])[CH2:15][C:16]#[C:17][C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1[NH2:4]

参加物

7

反応物 3

HCID 679892-Bromo-5-(trifluoromethyl)benzenamineHCID 81531DiisopropylethylamineHCID 81643N,N-Dimethylpropargylamine

生成物 1

HCID 684639942-(3-Dimethylamino-1-propynyl)-5-(trifluoromethyl)aniline

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

A resealable tube was charged with 2-bromo-5-(trifluoromethyl)aniline (1.00 g, 4.16 mmol), 1-dimethylamino-2-propyne (0.520 g, 6.20 mmol), PdCl2(PPh3)2 (0.15 g, 0.21 mmol), copper iodide (0.80 mg, 0.42 mmol), diisopropylethylamine (1.0 mL) and acetonitrile (3.0 mL). The system was purged with argon, the tube sealed and the mixture stirred at room temperature for 20 h. The reaction mixture was filtered through celite and concentrated. The residue was purified via column chromatography on silica gel (gradient elution with 0-10% methanol-dichloromethane) to afford 2-(3-dimethylamino-1-propynyl)-5-(trifluoromethyl)aniline as a brown oil. MS m/z=243 [M+H]+. Calc'd for C12H13F3N2: 242.

後処理

  1. customThe system was purged with argon
  2. customthe tube sealed
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationconcentrated
  5. customThe residue was purified via column chromatography on silica gel (gradient elution with 0-10% methanol-dichloromethane)

出典と根拠

ORDレコード
ord-ee99837cdf0c48098abafd0fcb1f1e71
出典データセット
uspto-grants-2010_08
特許番号
US07776869B2

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