Hydrochloric Acid → HCID 89553765, compound

HRID 590390Notes

Reaction equation

HRID 590390 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](C=O)=[CH:4]1.[Br:14][CH2:15][CH2:16][CH2:17]Br.Cl.CN([CH:23]=[O:24])C>O>[Br:14][CH2:15][CH2:16][CH2:17][N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:23]=[O:24])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide3×HCID 80011,3-DibromopropaneHCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 89553765HCID 89553765, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.70 g (30.31 mmol) of 60% sodium hydride suspension are added to 14 ml of anhydrous DMF and a solution of 2.40 g (16.53 mmol) of 1H-indole-3-carbaldehyde in 10 ml of DMF added dropwise. After 45 min of stirring at room temperature the solution is cooled externally with an ice/water bath and a solution of 2.52 ml (5.01 g; 24.80 mmol) of 1,3-dibromopropane in 6 ml of DMF added dropwise. The solution is stirred at room temperature for 2 hr before adding 10 ml of water and 10 ml of 2N HCl. The suspension is extracted thrice with ethyl ether, washed with water, dried and concentrated in vacuo. The residue is chromatographically purified (hexane to hexane/EtAcO 4:1) to give 1.4 g of the pure title compound (33% yield).

Workup

  1. temperatureis cooled externally with an ice/water bath
  2. stirringThe solution is stirred at room temperature for 2 hr
  3. extractionThe suspension is extracted thrice with ethyl ether
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographically purified (hexane to hexane/EtAcO 4:1)

Sources & evidence

ORD record
ord-43f18399416e491082d0018fab837546
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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