Tin tetrachloride → HCID 67995580, compound

HRID 2361383Notes

Reaction equation

HRID 2361383 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[Sn](Cl)(Cl)(Cl)Cl.[CH3:21][C:22]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>ClCCl.[N+](C)([O-])=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:24](=[O:25])[C:23]3[CH:27]=[CH:28][CH:29]=[C:30]([N+:31]([O-:33])=[O:32])[C:22]=3[CH3:21])=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 24287Tin tetrachlorideHCID 70094966-Bromo-1H-indole-2-carboxylic acid ethyl esterHCID 121948722-Methyl-3-nitrobenzoyl chloride

Product 1

HCID 67995580HCID 67995580, compoundYield 99.5%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 6375NitromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 6-bromo-1H-indole-2-carboxylate (4.40 g, 16.41 mmol) in dichloromethane (70 mL) at 0° C. was added tin (IV) chloride in dichloromethane (20.51 mL, 20.51 mmol) over 15 min. The resulting yellow heterogeneous mixture was stirred at room temperature for 30 min before a solution 2-methyl-3-nitrobenzoyl chloride (4.42 g, 22.16 mmol) in nitromethane (70 mL) was added over 20 min. The mixture was stirred at room temperature for 4 hr and then poured into ice-cold water (200 mL). The resulting mixture was stirred at room temperature for 20 min and diluted with ethyl acetate (800 ml). The mixture was washed with water (100 mL), saturated NaHCO3 solution (2×100 ml), water (100 mL), and brine (100 mL). The organic solution was dried over anhydrous MgSO4. Removal of solvent under vacuum gave the desired product (7.04 g, 16.33 mmol, 99% yield) as yellow solid.

Workup

  1. additionwas added over 20 min
  2. stirringThe resulting mixture was stirred at room temperature for 20 min
  3. washThe mixture was washed with water (100 mL), saturated NaHCO3 solution (2×100 ml), water (100 mL), and brine (100 mL)
  4. dry with materialThe organic solution was dried over anhydrous MgSO4
  5. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-5eaaa4dd82914f7ab1ffe14613a9686d
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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