Di-tert-butyl dicarbonate → Tert-butyl 4-formyl-1H-indole-1-carboxylate

HRID 551508Notes

Reaction equation

HRID 551508 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](C=O)[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C2C=CC=C([CH:28]=[O:29])C=2C=C1.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C>>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([CH:28]=[O:29])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 333703Indole-4-carboxaldehydeHCID 14616867Tert-butyl 6-formyl-1H-indole-1-carboxylate

Product 1

HCID 49758854Tert-butyl 4-formyl-1H-indole-1-carboxylate

Procedure

4-Formyl-indole-1-carboxylic acid tert-butyl ester was synthesized by a procedure similar to 6-Formyl-indole-1-carboxylic acid tert-butyl ester from starting materials 1H-Indole-4-carbaldehyde and di-tert-butyl-dicarbonate to yield the product as a clear yellow oil (2 g, 80%). LC-MS (ES) calculated for C14H15NO3, 245.1; found m/z 244 [M−H]−.

Sources & evidence

ORD record
ord-9d3c443274c54beaae18c111fb2ba63b
Source dataset
uspto-grants-2011_05
Patent number
US07947728B1

Reaction notes

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