Indole-5-carboxaldehyde → tert-Butyl 5-formyl-1H-indole-1-carboxylate

HRID 856994Notes

Reaction equation

HRID 856994 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)=[O:2].[C:12]([O:16][C:17](=O)[O:18]C(C)(C)C)([CH3:15])([CH3:14])[CH3:13]>CN(C)C1C=CN=CC=1.C(#N)C.CCOC(C)=O>[C:12]([O:16][C:17]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([CH:1]=[O:2])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 2

HCID 589040Indole-5-carboxaldehydeHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 11172622tert-Butyl 5-formyl-1H-indole-1-carboxylateYield 100%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Formylindole (1.45 g, 10.0 mmol) and 4-dimethylaminopyridine (1.47 g, 12.0 mmol) were dissolved in acetonitrile (20 mL) with stirring at ambient temperature. Once dissolution was complete, the reaction mixture was cooled to −10° C. with stirring. Di-t-butylcarbonate (2.18 g, 10.0 mmol) was added in one portion. Stirring was continued for 2 h. The reaction mixture was diluted with EtOAc (50 mL) and the organic solution was washed successively with water (20 mL), a 1N HCl solution (10 mL), a saturated NaHCO3 solution (20 mL) and brine (20 mL). The organic solution was dried over MgSO4 and filtered. Solvent was removed in vacuo from the filtrate to provide a pale yellow oil (2.45 g, 100% yield): 1H NMR (CDCl3, 300 MHz): 10.1 (s, 1H), 8.31 (d, 1H, J=8), 8.12 (s, 1H), 7.87 (dd, 1H, J=8, 1), 7.70 (d, 1H, J=4), 6.71 (d, 1H, J=4), 1.71 (s, 9H).

Workup

  1. dissolutionOnce dissolution
  2. temperaturethe reaction mixture was cooled to −10° C.
  3. stirringwith stirring
  4. stirringStirring
  5. washthe organic solution was washed successively with water (20 mL)
  6. dry with materialThe organic solution was dried over MgSO4
  7. filtrationfiltered
  8. customSolvent was removed in vacuo from the filtrate

Sources & evidence

ORD record
ord-7b261bd08c0340918d63f9bdb90b0cc1
Source dataset
uspto-grants-2006_12
Patent number
US07144894B2

Reaction notes

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