Triethylamine → tert-butyl 6-bromo-3-formyl-1H-indole-1-carboxylate

HRID 2425329Notes

Reaction equation

HRID 2425329 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:13]([O:17][C:18](Cl)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>C(Cl)Cl>[C:13]([O:17][C:18]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=2)[C:6]([CH:11]=[O:12])=[CH:7]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27948306-Bromoindole-3-carbaldehydeHCID 9920397Tert-butyl Chloroformate

Product 1

HCID 11313330tert-butyl 6-bromo-3-formyl-1H-indole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-Bromoindole-3-carboxaldehyde, 23 (5.0 g, 22.3 mmol) is dissolved in methylene chloride (40 mL), then cooled to 0° C. and tert-butylchloroformate (3.40 g, 25.0 mmol) and triethyl amine (2.50 g, 25.0 mmol) are added over 5 minutes. The reaction is maintained at reflux, under inert atmosphere for 3 hours. The reaction is cooled, filtered and the solvent removed in vacuo. The residue composed primarily of compound 24 is used in the Example 18 without purification. (See, e.g., G. Wille and W. Steglich, Synthesis, 2001, 759-762 for a related procedure.)

Workup

  1. temperatureThe reaction is maintained
  2. temperatureat reflux, under inert atmosphere for 3 hours
  3. temperatureThe reaction is cooled
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customis used in the Example 18 without purification
  7. customSteglich, Synthesis, 2001, 759-762 for a related procedure

Sources & evidence

ORD record
ord-69c6fc11f5f84bed94d17a7a0a8b8255
Source dataset
uspto-grants-2011_06
Patent number
US07964649B2

Reaction notes

Loading…