Aluminum(III) Chloride → HCID 66898634, compound

HRID 2168482Notes

Reaction equation

HRID 2168482 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[NH:7][C:6]([Si](C)(C)C)=[C:5]2[CH3:19].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH3:19]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 66898238HCID 66898238, compound

Product 1

HCID 66898634HCID 66898634, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 5-chloro-3-methyl-2-(trimethylsilyl)-1H-indole-7-carboxylate (510 mg, 1.73 mmol) from Step A above and aluminum chloride (254 mg, 1.9 mmol) were added to methylene chloride (5 mL) and the reaction mixture was stirred for 3 h at 0° C. The reaction was quenched with water, extracted with ether, dried over sodium sulfate, filtered, and concentrated to afford methyl 5-chloro-3-methyl-1H-indole-7-carboxylate (410 mg, quantitative yield) as a dark green solid: 1H NMR (500 MHz, CDCl3) δ 8.09 (s, 1H), 8.01 (d, J=1.0 Hz, 1H), 7.87 (d, J=1.0 Hz, 1H), 4.01 (s, 3H), 3.40 (s, 3H); MS (ESI+) m/z 224 (M+H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ether
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-526d030d128f40c890b7e0e592e151f7
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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