1H-Indole-5-Carboxylic Acid → Tert-butyl 1H-indole-5-carboxylate

HRID 1810099Notes

Reaction equation

HRID 1810099 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(NC(=NC(C)C)O[C:19]([CH3:22])([CH3:21])[CH3:20])(C)C>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 742801H-Indole-5-Carboxylic AcidHCID 110417822-tert-Butyl-1,3-diisopropylisourea

Product 1

HCID 11183550Tert-butyl 1H-indole-5-carboxylateYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Indole-5-carboxylic acid (1.00 g, 6.21 mmol) and tert-butyl N,N′-diisopropylcarbamimidate 2.29 g) were combined in 15 mL of THF and the reaction mixture was stirred for 25 hours. The reaction mixture was concentrated and the residue was purified on a silica gel column eluting with a gradient of 5% ethyl acetate/hexane to 100% ethyl acetate to provide tert-butyl 1H-indole-5-carboxylate (0.800 g, 3.68 mmol, 59%.)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified on a silica gel column
  3. washeluting with a gradient of 5% ethyl acetate/hexane to 100% ethyl acetate

Sources & evidence

ORD record
ord-4a243d6eff5944e99f9738e46a422afc
Source dataset
uspto-grants-2013_01
Patent number
US08362056B2

Reaction notes

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