Phenylacetylene → 5-Nitro-3-(phenylethynyl)pyridin-2-amine

HRID 2196670노트

반응식

HRID 2196670 반응식
Br[C:2]1[C:3]([NH2:11])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)#[CH:13]>[Cu]I.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>[N+:8]([C:6]1[CH:7]=[C:2]([C:13]#[C:12][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]([NH2:11])=[N:4][CH:5]=1)([O-:10])=[O:9]

참가 물질

5

반응물 2

HCID 10821PhenylacetyleneHCID 27344122-Amino-3-bromo-5-nitropyridine

생성물 1

HCID 593229015-Nitro-3-(phenylethynyl)pyridin-2-amine수율 50%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매

실험 절차

A solution of 3-bromo-5-nitropyridin-2-amine (655 mg, 3.0 mmol, 1.0 eq.) in 1:1 TEA/DMF (40 mL) was degassed with argon for 10 minutes, and ethynylbenzene (1.5 eq.), CuI (0.04 eq.), and PdCl2(PPh3)2 (0.04 eq.) were sequentially added. The mixture was degassed with argon for 10 minutes, and then stirred at room temperature for 16 hours. The volatiles were removed under reduced pressure, and CH2Cl2 (25 mL) was added. The mixture was sonicated for 15 minutes, cooled to 0° C., and collected by vacuum filtration to afford 5-nitro-3-(phenylethynyl)pyridin-2-amine (356 mg, 50%).

후처리

  1. customThe mixture was degassed with argon for 10 minutes
  2. customThe volatiles were removed under reduced pressure, and CH2Cl2 (25 mL)
  3. additionwas added
  4. customThe mixture was sonicated for 15 minutes
  5. temperaturecooled to 0° C.
  6. filtrationcollected by vacuum filtration

출처 및 근거

ORD 기록
ord-59cf437319694310ba6ab629fde7002c
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338452B2

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