1-Bromopentane → 1-Pentyl-7-azaindole

HRID 1715206Notes

Reaction equation

HRID 1715206 reaction equation
[H-].[Na+].[NH:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[CH:4]1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>CN(C)C=O>[CH2:13]([N:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[CH:4]1)[CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 24758Sodium hydride

Product 1

HCID 162039651-Pentyl-7-azaindoleYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride in anhydrous N,N-dimethylformamide (40.0 mL) was added 1H-pyrrolo[2,3-b]pyridine (5.00 g, 42.4 mmol) at 0° C. The reaction mixture was stirred for 0.5 h, followed by the addition of 1-bromopentane (9.25 g, 61.2 mmol). The reaction mixture was stirred at ambient temperature for 3.5 h, quenched with water (20.0 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers was washed with water (3×50.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness to give the title compound (8.00 g, 100%) as a pale yellow oil: 1H NMR (300 MHz, CDCl3) δ 8.29 (dd, 1H), 7.86 (d, 1H), 7.19 (d, 1H), 7.02-6.98 (m, 1H), 6.41 (d, 1H), 4.25 (t, 2H), 1.89-1.79 (m, 2H), 1.35-1.25 (m, 4H), 0.85 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 147.4, 142.6, 128.6, 127.9, 120.6, 115.5, 99.2, 44.6, 30.1, 29.0, 22.4, 13.9.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 3.5 h
  2. customquenched with water (20.0 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layers was washed with water (3×50.0 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-a3d413b019274c3e8ac89ecbc74a2930
Source dataset
uspto-grants-2010_09
Patent number
US07799798B2

Reaction notes

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