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Diethyl Carbonate → ethyl 6-fluoro-1-(triisopropylsilyl)-1H-indole-5-carboxylate

HRID 336823
Notes
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Reaction equation

HRID 336823 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.C([Li])(CC)C.[C:26](=O)([O:30]CC)[O:27][CH2:28][CH3:29].[Cl-].[NH4+]>O1CCCC1>[C:26]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[F:1])[N:8]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:18]([CH3:20])[CH3:19])[CH:12]([CH3:13])[CH3:14])[CH:7]=[CH:6]2)([O:27][CH2:28][CH3:29])=[O:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7766Diethyl CarbonateHCID 25517Ammonium ChlorideHCID 117162536-fluoro-1-[tris(propan-2-yl)silyl]-1H-indoleHCID 178418400CID 53628100

Product 1

HCID 67074085ethyl 6-fluoro-1-(triisopropylsilyl)-1H-indole-5-carboxylateYield 46.9%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 760 mg (2.61 mmol) of 6-fluoro-1-triisopropylsilylindole dissolved in 6 ml of anhydrous tetrahydrofuran are added dropwise at −78° C. under argon 2.01 ml of a sec-butyllithium solution (1.3M in cyclohexane, 2.01 mmol). The reaction mixture is stirred for 2 h at −78° C. then 500 μL (3.15 mmol) of diethyl carbonate are added dropwise at −78° C. to the reaction mixture. This mixture is stirred for 5 h with a gentle temperature rise then an ammonium chloride saturated aqueous solution is added. The product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, and concentrated. The residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 97:3) to yield 445 mg (46%) of 5-carboethoxy-6-fluoro-1-triisopropylsilylindole in the form of a colourless oil.

Workup

  1. stirringThis mixture is stirred for 5 h with a gentle temperature rise
  2. extractionThe product is extracted several times with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 97:3)

Sources & evidence

ORD record
ord-d65a3426479a4ba0809f4a699a88bc45
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889711B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes