Dimethylformamide → 5-bromo-6-methyl-1H-indole-3-carbaldehyde

HRID 338294Notes

Reaction equation

HRID 338294 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[CH3:16])[NH:12][CH:11]=[CH:10]2.[OH-].[Na+].CN([CH:22]=[O:23])C>>[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[CH3:16])[NH:12][CH:11]=[C:10]2[CH:22]=[O:23]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 247292415-bromo-6-methyl-1H-indole

Product 1

HCID 823888555-bromo-6-methyl-1H-indole-3-carbaldehydeYield 85%

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (0.73 g, 4.79 mmol) and DMF (5.0 mL) were mixed together and stirred for 5 min. A solution of 5-bromo-6-methyl-1H-indole (500 mg, 2.39 mmol) in DMF (3.0 mL) was added to the solution slowly and complete solid was formed which stopped stirring. The solution was adjusted to pH=10 with 1N NaOH, then heated to 100° C. for 1 min. The reaction was cooled to room temperature. The precipitated solids were filtered and dried to give the title compound (480 mg, 85%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.2 (s, 1H), 9.88 (s, 1H), 8.28 (s, 1H), 8.23 (s, 1H), 7.49 (s, 1H), 2.44 (s, 3H).

Workup

  1. customcomplete solid was formed which
  2. stirringstopped stirring
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationThe precipitated solids were filtered
  5. customdried

Sources & evidence

ORD record
ord-eec0d9430b6e4b479210a1d9521d12f4
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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