Dimethylformamide → 1H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-

HRID 2114066Notes

Reaction equation

HRID 2114066 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)N[N:8]=[CH:7]2.[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18]Cl.C[N:23](C=O)C>[Cl-].[Na+].O>[Br:3][C:4]1[CH:5]=[C:6]2[CH:10]=[CH:11][N:8]([CH2:18][O:17][CH2:16][CH2:15][Si:14]([CH3:21])([CH3:20])[CH3:13])[C:7]2=[N:23][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 7619295-bromo-1H-indazoleHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 598250161H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-Yield 90%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (60% suspension in oil, 0.305 g, 7.63 mmol) was added to a stirred solution of 5-bromo-7-azaindole 24 (1.00 g, 5.08 mmol) in DMF (10 mL). After the mixture was stirred for 30 min, 2-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl; 1.35 mL, 7.63 mmol) was added. The mixture was stirred for 2.5 days and poured into brine and extracted with AcOEt. The organic layer was washed with brine twice, dried (MgSO4), and concentrated. The residue was purified by means of SGC with hexane:AcOEt as eluent to afford 51 (1.50 g, 90%) as a tan syrup. 1H NMR (400 MHz, CDCl3) δ 0.00 (s, 9H), 0.94-0.99 (m, 2H), 3.53-3.61 (m, 2H), 5.71 (s, 2H), 6.53 (d, J=0.36 Hz, 1H), 7.42 (d, J=0.36 Hz, 1H), 8.09 (d, J=0.22 Hz, 1H), 8.42 (d, J=0.22 Hz, 1H).

Workup

  1. stirringThe mixture was stirred for 2.5 days
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with brine twice
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by means of SGC with hexane

Sources & evidence

ORD record
ord-71bafad0f2db499485acc257993b991d
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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