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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
Notes
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Reaction equation

HRID 245775 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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, compound

Product 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-carboxamideYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-bbd0b44c3fb74cf19ccfc43c49ec8ea0
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658794B2

Reaction notes

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