1-Bromopropane → HCID 86723161, compound

HRID 868874Notes

Reaction equation

HRID 868874 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[N+:17]([O-:19])=[O:18].Br[CH2:21][CH2:22][CH3:23]>C(#N)C>[F:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:21][CH2:22][CH3:23])[CH:12]=[C:11]2[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 86723162HCID 86723162, compound

Product 1

HCID 86723161HCID 86723161, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (1.5 g, 11.1 mmol) was added to a solution of 5-fluoro-3-nitro-indole (1.0 g, 5.6 mmol) and 1-bromo-propane (820 mg, 6.7 mmol) in ACN (20 mL) at rt. The reaction was heated to 80° C. and stirred overnight. The solution was filtered and concentrated, and the residue was purified by silica gel chromatography to give 520 mg (42%) of the title compound as a brown solid. 1H NMR (400 MHz, DMSO-d6): δ 0.86 (3H, t, J=7.2 Hz), 1.81-1.87 (2H, m), 4.30 (2H, t, J=7.2 Hz), 7.28 (1H, td, J=2.4, 9.2 Hz), 7.77-7.86 (2H, m), 8.84 (1H, s).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-045fcb2050864a70b85687262de3e6b5
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

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