Water → 5-(2,6-Diethyl-Phenyl)-1-(1-Propyl-Butyl)-1H-Pyrrolo[2,3-C]Pyridine

HRID 472021Notes

Reaction equation

HRID 472021 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2].[H-].[Na+].Br[CH:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26].O>CN(C=O)C.CCOC(C)=O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][N:17]([CH:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[C:14]2=[CH:15][N:16]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 704604-BromoheptaneHCID 116732465-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 116817955-(2,6-Diethyl-Phenyl)-1-(1-Propyl-Butyl)-1H-Pyrrolo[2,3-C]Pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (32 mg, 0.13 mmol) in DMF (0.5 mL) is added NaH (95%, 6 mg). The reaction mixture is stirred at room temperature for 30 minutes, and 4-bromo-heptane (137 mg, 0.77 mmol) is added. The mixture is heated at 60° C. for three hours and cooled. To the mixture, water (2 mL) and EtOAc (2 mL) are added. The organic layer is separated, washed with water once and concentrated under reduced pressure. The residue is purified by PTLC (Hexane/EtOAc 4:1) to give the titled compound. 1H NMR: (CDCl3) 8.82 (s, 1H), 7.43 (s, 1H), 7.32 (d, 1H), 7.31 (t, 1H), 7.16 (d, 2H), 6.87 (s, 1H), 6.53 (d, 1H), 4.42 (m, 1H), 2.32-2.40 (m, 4H), 1.86-1.95 (m, 4H), 1.15-1.32 (m, 4H), 1.03 (t, 6H), 0.84 (m, 6H).

Workup

  1. temperatureThe mixture is heated at 60° C. for three hours
  2. temperaturecooled
  3. customThe organic layer is separated
  4. washwashed with water once
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by PTLC (Hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-b23f2140518446078bc89404aca994c1
Source dataset
uspto-grants-2014_01
Patent number
US08633193B2

Reaction notes

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