Nitrogen → 6-Chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine

HRID 513064

반응식

HRID 513064 반응식
[Cl:1][C:2]1[N:7]=[C:6](I)[C:5]([NH2:9])=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:17][C:18]([CH3:22])([CH3:21])[C:19]#[CH:20].N#N>C1(C)C=CC=CC=1.O.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>[Cl:1][C:2]1[N:7]=[C:6]([C:20]#[C:19][C:18]([CH3:22])([CH3:21])[CH3:17])[C:5]([NH2:9])=[CH:4][CH:3]=1

참가 물질

9

반응물 4

HCID 947NitrogenHCID 8471TriethylamineHCID 135123,3-Dimethyl-1-butyneHCID 184070436-Chloro-2-iodopyridin-3-amine

생성물 1

HCID 579081596-Chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine수율 88%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
70 °C

실험 절차

To a solution of 6-chloro-2-iodo-pyridin-3-ylamine (16.0 g, 62.7 mmol) in toluene (160 mL) and water (80 mL) were added Et3N (12.7 g, 125 mmol), Pd(PPh3)2Cl2 (2.2 g, 3.1 mmol), CuI (238 mg, 1.3 mmol) and 3,3-dimethyl-but-1-yne (7.7 g, 94 mmol) successively under N2 atmosphere. The reaction mixture was heated at 70° C. for 3 hours and was allowed to cool to room temperature. The resulting mixture was extracted with ethyl acetate (150 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give 6-chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine (11.5 g, 88%), which was used in the next step without further purification.

후처리

  1. temperatureto cool to room temperature
  2. extractionThe resulting mixture was extracted with ethyl acetate (150 mL×3)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-29912d0aa2fd4ab58c1462a8712a01bd
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102672B2

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