Dimethylformamide → 2,3-Dimethyl-1H-pyrrolo[2,3-c]pyridine

HRID 400609

반응식

HRID 400609 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][C:9]#[C:10][CH3:11].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].C[N:21](C=O)C>C(OCC)(=O)C.[Cl-].[NH4+].C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CO>[CH3:8][C:9]1[NH:21][C:7]2=[CH:2][N:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH3:11]

참가 물질

11

반응물 5

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 10419DimethylacetyleneHCID 2211262-IodopyridineHCID 433294Lithium Chloride

생성물 1

HCID 600268282,3-Dimethyl-1H-pyrrolo[2,3-c]pyridine수율 77%

시약·촉매·용매 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 887Methanol용매HCID 6344Dichloromethane용매3회HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

반응 조건

온도
90 °C

실험 절차

In a pressure tube, a solution of iodopyridine (1.80 g, 8.18 mmol) in 20 mL of DMF was treated with 2-butyne (1.5 mL, 19.1 mmol), Pd(dppf)2Cl2.CH2Cl2 (357 mg, 0.438 mmol), lithium chloride (367 mg, 8.71 mmol), and sodium carbonate (1.82 g, 17.2 mmol). The tube was sealed and heated to 90° C. After 24 hours, the tube was cooled and opened. The resulting mixture was diluted with 20 mL of ethyl acetate and 20 mL of saturated aqueous ammonium chloride solution. The phases were separated and the aqueous layer was extracted with three 50 mL portions of ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient) afforded the title product as a brown solid (920 mg, 77% yield).

후처리

  1. customThe tube was sealed
  2. temperaturethe tube was cooled
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with three 50 mL portions of ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1b885b6059d946be93d874fc01006f08
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

연결된 노트

불러오는 중…