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

HRID 400609

反応式

HRID 400609 の反応式
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]

参加物

11

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒3 回HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1b885b6059d946be93d874fc01006f08
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

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