Benzoyl chloride, 3,4,5-trimethoxy- → (6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone

HRID 273329Notes

Reaction equation

HRID 273329 reaction equation
C([Mg]Br)C.[CH3:5][C:6]1[N:11]=[C:10]2[NH:12][CH:13]=[CH:14][C:9]2=[CH:8][CH:7]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[C:20](Cl)=[O:21].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[CH3:5][C:6]1[N:11]=[C:10]2[NH:12][CH:13]=[C:14]([C:20]([C:19]3[CH:23]=[C:24]([O:28][CH3:29])[C:25]([O:26][CH3:27])=[C:17]([O:16][CH3:15])[CH:18]=3)=[O:21])[C:9]2=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 6451240Aluminum(III) ChlorideHCID 114577166-Methyl-1H-pyrrolo[2,3-b]pyridineHCID 178418443HCID 178418443, compound

Product 1

HCID 52951496(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-(3,4,5-trimethoxy-phenyl)-methanoneYield 48%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Ethylmagnesium bromide (3.0 M solution in diethyl ether, 0.43 mL) was added to a mixture of 6-methyl-1H-pyrrolo[2,3-b]pyridine (0.127 g, 0.969 mmol) and anhydrous zinc chloride (0.263 g, 1.94 mmol) in dry CH2Cl2 (20 mL) over 10 min at room temperature. The suspension was stirred for 1 h and then a solution of 3,4,5-trimethoxybenzoyl chloride (0.335 g, 1.45 mmol) in dry CH2Cl2 (10 mL) was added dropwise over 5 min. After 1 h, aluminum chloride (0.129 g, 0.969 mmol) was added. The resulting thick mixture was vigorously stirred for 5 h. The reaction was quenched with water (10 mL) and extracted with CH2Cl2 (20 mL). The organic layer was dried over anhydrous MgSO4 and concentrated to give a brown oil, which was further purified on a silica gel column (MeOH:CH2Cl2=1:25) to give compound 8 (0.150 g, 48%) as a white solid.

Workup

  1. waitAfter 1 h
  2. stirringThe resulting thick mixture was vigorously stirred for 5 h
  3. customThe reaction was quenched with water (10 mL)
  4. extractionextracted with CH2Cl2 (20 mL)
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customto give a brown oil, which
  8. customwas further purified on a silica gel column (MeOH:CH2Cl2=1:25)

Sources & evidence

ORD record
ord-0ded42642092427784632e5d53a0c93c
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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