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Imidazole → Methyl 2-(1,3-benzodioxol-5-yl)-2-[1-methyl-6-(triisopropylsilyloxymethyl)-1H-3-indolyl]acetate

HRID 381323
Notes
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Reaction equation

HRID 381323 reaction equation
Cl[Si:2]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4].[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH:21]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([CH2:35][OH:36])=[CH:32][CH:33]=4)[N:28]([CH3:37])[CH:27]=3)[C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:15]=2[O:14][CH2:13]1.N1C=CN=C1>CN(C)C=O>[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH:21]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([CH2:35][O:36][Si:2]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4])=[CH:32][CH:33]=4)[N:28]([CH3:37])[CH:27]=3)[C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:15]=2[O:14][CH2:13]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 22467201Methyl 2-(1,3-benzodioxol-5-yl)-2-[6-(hydroxymethyl)1-methyl-1H-3-indolyl]acetate

Product 1

HCID 22467250Methyl 2-(1,3-benzodioxol-5-yl)-2-[1-methyl-6-(triisopropylsilyloxymethyl)-1H-3-indolyl]acetateYield 80.9%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Chlorotriisopropylsilane (0.19 ml, 0.88 mmol) was added to a solution of methyl 2-(1,3-benzodioxol-5-yl)-2-[6-(hydroxymethyl)-1-methyl-1H-3-indolyl]acetate (from step (d), 260 mg, 0.74 mmol) and imidazole (100 mg, 1.47 mmol) in anhydrous dimethylformamide (3 ml). After 3 hours the mixture was partitioned between diethyl ether and water, the organic layer was separated and washed with water. The organic layer was dried (magnesium sulphate), and the solvent removed in vacuo. The residue was flash chromatographed (using 50% dichloromethane, 50% hexane as eluent) to give the subtitle compound (305 mg) as an oil.

Workup

  1. customAfter 3 hours the mixture was partitioned between diethyl ether and water
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialThe organic layer was dried (magnesium sulphate)
  5. customthe solvent removed in vacuo
  6. customchromatographed (using 50% dichloromethane, 50% hexane as eluent)

Sources & evidence

ORD record
ord-3ee36ad7a45542b49ffcc7e4148e0ee4
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06306852B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes