Benzoyl chloride, 3,4,5-trimethoxy- → HCID 52951492, compound

HRID 273332Notes

Reaction equation

HRID 273332 reaction equation
C([Mg]Br)C.[CH3:5][O:6][C:7]1[N:12]=[C:11]2[NH:13][CH:14]=[CH:15][C:10]2=[CH:9][CH:8]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[C:21](Cl)=[O:22].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[CH3:5][O:6][C:7]1[N:12]=[C:11]2[NH:13][CH:14]=[C:15]([C:21]([C:20]3[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:18]([O:17][CH3:16])[CH:19]=3)=[O:22])[C:10]2=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 6451240Aluminum(III) ChlorideHCID 116151916-Methoxy-1H-pyrrolo[2,3-b]pyridineHCID 178418443HCID 178418443, compound

Product 1

HCID 52951492HCID 52951492, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Ethylmagnesium bromide (3.0 M solution in diethyl ether, 0.33 mL) was added to a mixture of 6-methoxy-1H-pyrrolo[2,3-b]pyridine (0.108 g, 0.73 mmol) and anhydrous zinc chloride (0.201 g, 1.46 mmol) in dry CH2Cl2 (20 mL) over 10 min at room temperature. The suspension was stirred for 1 h and 3,4,5-trimethoxybenzoyl chloride (0.252 g, 1.09 mmol) in dry CH2Cl2 (10 mL) was then added dropwise over 5 min. After the reaction mixture was stirred for 1 h, aluminum chloride (0.097 g, 0.73 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 combined organic layers were dried over anhydrous MgSO4 and evaporated to give a brown oil, which was purified on a silica gel column eluting with EtOAc/hexane (1:1) to compound 9 (0.189 g, 76%).

Workup

  1. stirringAfter the reaction mixture was stirred for 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 combined organic layers were dried over anhydrous MgSO4
  6. customevaporated
  7. customto give a brown oil, which
  8. customwas purified on a silica gel column
  9. washeluting with EtOAc/hexane (1:1) to compound 9 (0.189 g, 76%)

Sources & evidence

ORD record
ord-e519468a307e42f28efba777c5dc65c2
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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