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

HRID 502762

반응식

HRID 502762 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ee99837cdf0c48098abafd0fcb1f1e71
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776869B2

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