Ethyl Acetate → 4-Methoxy-7-pyrazinyl-6-azaindol-3-yl-oxoacetic acid methyl ester

HRID 606744노트

반응식

HRID 606744 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:15]=[N:14][C:13]([C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.C([O-])(=[O:24])C.[NH4+].C[CH2:28][O:29][C:30]([CH3:32])=[O:31]>C(Cl)Cl.C[N+]([O-])=O>[CH3:28][O:29][C:30](=[O:31])[C:32]([C:9]1[C:8]2[C:12](=[C:13]([C:16]3[CH:21]=[N:20][CH:19]=[CH:18][N:17]=3)[N:14]=[CH:15][C:7]=2[O:6][CH3:5])[NH:11][CH:10]=1)=[O:24]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 6451240Aluminum(III) ChlorideHCID 207912514-Methoxy-7-(pyrazin-2-YL)-1H-pyrrolo[2,3-C]pyridine

생성물 1

HCID 670462744-Methoxy-7-pyrazinyl-6-azaindol-3-yl-oxoacetic acid methyl ester수율 68%

시약·촉매·용매 1

HCID 23431834Dichloromethane nitromethane용매

실험 절차

To a mixture of AlCl3 (3.09 g, 23.2 mmol) in 20 mL of CH2Cl2-MeNO2 (4:1) was added 4-methoxy-7-pyrazinyl-6-azaindole (0.525 g, 2.32 mmol) as a solid. To the resulting burgundy solution was added methyl oxalyl chloride (0.853 mL, 9.28 mmol) dropwise and then the mixture was stirred at room temperature for 1.5 h. The reaction mixture was then carefully poured into cold 20% aqueous ammonium acetate and EtOAc was added. The resulting emulsion was filtered and the residue was washed with additional EtOAc. The organic phase was separated and the aqueous phase was again extracted with EtOAc. The combined organic phase was dried (MgSO4) and evaporated to give 4-methoxy-7-pyrazinyl-6-azaindol-3-yl-oxoacetic acid methyl ester (0.494 g, 68%) as a brownish solid: LCMS m/e 313 (M+H)+. This material (0.456 g, 1.46 mmol) was taken up in 20 mL of MeOH, 1M K2CO3 (5.84 mL, 5.84 mmol) was added and the mixture was stirred at room temperature for 30 min. The solution was then diluted with water (4 mL) and concentrated in vacuo. The resulting aqueous solution was cooled at 0° C. and acidified to pH 1-2 with 6N HCl. This gave a bright yellow precipitate which was filtered, washed with cold 0.1N HCl and ether and dried in vacuo to give the title compound (0.309 g, 71%) as a yellow solid:

후처리

  1. additionwas added
  2. filtrationThe resulting emulsion was filtered
  3. washthe residue was washed with additional EtOAc
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was again extracted with EtOAc
  6. dry with materialThe combined organic phase was dried (MgSO4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-ccd74fd4e3534916bae17c604218cb87
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915283B2

반응 노트

불러오는 중…