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2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → 5-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

HRID 245775
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HRID 245775 반응식
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)[CH:7]=[CH:6][C:4]=1[NH2:5].C([Mg]Cl)C.[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[CH:33]=[C:32]([C:34](OC)=[O:35])[N:31]([CH3:38])[C:28]2=[CH:29][N:30]=1>O1CCCC1>[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[CH:33]=[C:32]([C:34]([NH:5][C:4]3[CH:6]=[CH:7][C:8]([B:10]4[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]4)=[CH:9][C:3]=3[O:2][CH3:1])=[O:35])[N:31]([CH3:38])[C:28]2=[CH:29][N:30]=1
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참가 물질

5

반응물 3

HCID 177502072-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 67366332methyl 5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylateHCID 178461633HCID 178461633, 화합물

생성물 1

HCID 673637125-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide수율 60.2%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
3회

실험 절차

To 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.09 g, 8.37 mmol) in tetrahydrofuran (20 ml) under a nitrogen atmosphere was added ethylmagnesium chloride, 2.0 M in tetrahydrofuran (4.19 ml, 8.37 mmol) and the mixture was heated at reflux for one hour. To the warm reaction was added methyl 5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (878 mg, 3.99 mmol) in tetrahydrofuran (10 ml) and the resulting mixture was heated overnight. Then the reaction mixture was cooled to room temperature and concentrated. The residue was taken up in ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was coated on hydromatrix and purified by flash chromatography (gradient of heptane to heptane/ethyl acetate 1/1) to give 5-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (1.05 g).

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for one hour
  3. customTo the warm reaction
  4. temperaturethe resulting mixture was heated overnight
  5. concentrationconcentrated
  6. washwashed with water
  7. extractionThe aqueous layer was extracted with ethyl acetate twice
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. custompurified by flash chromatography (gradient of heptane to heptane/ethyl acetate 1/1)

출처 및 근거

ORD 기록
ord-bbd0b44c3fb74cf19ccfc43c49ec8ea0
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658794B2

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