1-Bromopropane → HCID 4425595, compound

HRID 921005Notes

Reaction equation

HRID 921005 reaction equation
Br[CH2:2][CH2:3][CH3:4].[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:2][CH2:3][CH3:4])[CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 10796Cesium carbonateHCID 249055-Bromoindole

Product 1

HCID 4425595HCID 4425595, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1-Bromopropane (1.25 g, 10.2 mmol) was added to a solution of 5-bromo indole (2 g, 10.2 mmol) in DMF (30 mL) followed by cesium carbonate (6.63 g, 20.4 mmol), and the mixture was stirred at 100° C. for 2 h. Insoluble solids were filtered off, and filtrate was concentrated. Residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using 5% ethyl acetate in hexane as eluent to afford title compound (1.8 g, 74%) as oil. 1H NMR (400 MHz, CDCl3): δ 7.74 (d, J=1.6 Hz, 1H), 7.28 (m, 1H), 7.20 (m, 1H), 7.09 (d, J=3.2 Hz, 1H), 6.41 (d, J=2.4 Hz, 1H), 4.05 (t, J=7.2 Hz, 2H), 1.87 (m, 2H), 0.9 (t, J=7.2 Hz, 3H); ESI-MS m/z=238 (M+H)+.

Workup

  1. filtrationInsoluble solids were filtered off
  2. concentrationfiltrate was concentrated
  3. customResidue was partitioned between ethyl acetate and water
  4. customOrganic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-12d115497a01411b9428c4748e700db0
Source dataset
uspto-grants-2016_03
Patent number
US09273069B2

Reaction notes

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