Methanol → HCID 22718730, compound

HRID 1582645Notes

Reaction equation

HRID 1582645 reaction equation
C[Si](I)(C)C.[CH2:6]([O:8][C:9]([C:11]1[N:12]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[C:13]2[C:18]([CH:19]=1)=[C:17]([Cl:20])[C:16]([O:21]C)=[CH:15][CH:14]=2)=[O:10])[CH3:7].CO>C(Cl)(Cl)Cl>[Cl:31][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=1[Cl:30])[CH2:23][N:12]1[C:13]2[C:18](=[C:17]([Cl:20])[C:16]([OH:21])=[CH:15][CH:14]=2)[CH:19]=[C:11]1[C:9]([O:8][CH2:6][CH3:7])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 22718721HCID 22718721, compound

Product 1

HCID 22718730HCID 22718730, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trimethylsilyliodide (0.6 ml) was added to a solution of ethyl-N-(3,4-dichlorobenzyl)-4-chloro-5-methoxyindole-2-carboxylate (190 mg) in chloroform (20 ml). The mixture was heated to 50 C. for 18 hours then poured into methanol (50 ml) and concentrated under vacuo. The residue was purified by column chromatography using isohexane-20% ethyl acetate/isohexane as eluent to yield the product as a yellow solid (100 mg,71%) NMR: δ (CDCl3) 1.39 (t, 3H), 4.35 (q, 2H), 5.72 (s, 2H), 6.84 (dd, 1H), 7.05-7.13 (m, 3H) 7.3 (d, 1H) 7.35 (s, 1H);m/z396.2/398.2 (M−H+)

Workup

  1. temperatureThe mixture was heated to 50 C
  2. concentrationconcentrated under vacuo
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4055ffbcd2654d9eaac909fba13e2dac
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

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